# Electronic Supplementary Material (ESI) for Materials Advances.
# This journal is © The Royal Society of Chemistry 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1972046'
loop_
_audit_author_name
_audit_author_address
'Rekha Kumari'
;ICER SSCU IISc Bangalore Karnataka
India
;
_audit_update_record             
;
2023-11-04 deposited with the CCDC.	2024-02-26 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            'C17 H16 N2 O3'
_chemical_formula_weight         296.32

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                   5.7695(2)
_cell_length_b                   8.7640(3)
_cell_length_c                   14.5821(5)
_cell_angle_alpha                90
_cell_angle_beta                 98.449(3)
_cell_angle_gamma                90
_cell_volume                     729.33(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4689
_cell_measurement_theta_min      3.5690
_cell_measurement_theta_max      26.6660

_exptl_crystal_description       Plate
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_F_000             312
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.094
_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      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Xcalibur, Eos, Nova'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11140
_diffrn_reflns_av_unetI/netI     0.0281
_diffrn_reflns_av_R_equivalents  0.0269
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.570
_diffrn_reflns_theta_max         27.477
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3340
_reflns_number_gt                2771
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.876
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    0.998

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_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)+(0.0415P)²+0.0362P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1015 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -1.1(6)
_chemical_absolute_configuration unknown
_refine_ls_number_reflns         3340
_refine_ls_number_parameters     215
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0512
_refine_ls_R_factor_gt           0.0406
_refine_ls_wR_factor_ref         0.0976
_refine_ls_wR_factor_gt          0.0880
_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
H1 H 0.005(8) 0.070(5) 0.493(3) 0.110(13) Uiso 1 1 d . . . . .
H2A H 0.610(5) 0.237(4) 0.975(2) 0.074(10) Uiso 1 1 d . . . . .
H7 H 0.375(5) 0.328(4) 0.4398(19) 0.067(8) Uiso 1 1 d . . . . .
H15 H 1.027(4) 0.317(3) 0.9746(16) 0.051(7) Uiso 1 1 d . . . . .
C1 C 0.0680(4) 0.2337(3) 0.37072(18) 0.0506(6) Uani 1 1 d . . . . .
C2 C -0.1207(5) 0.1347(3) 0.37572(18) 0.0566(7) Uani 1 1 d . . . . .
C3 C -0.3031(5) 0.1271(4) 0.3017(2) 0.0701(9) Uani 1 1 d . . . . .
H3 H -0.429093 0.062285 0.305138 0.084 Uiso 1 1 calc R U . . .
C4 C -0.2988(5) 0.2137(4) 0.2241(2) 0.0669(8) Uani 1 1 d . . . . .
H4 H -0.422404 0.208157 0.175497 0.080 Uiso 1 1 calc R U . . .
C5 C -0.1122(5) 0.3095(4) 0.2174(2) 0.0671(8) Uani 1 1 d . . . . .
H5 H -0.108804 0.367339 0.164169 0.081 Uiso 1 1 calc R U . . .
C6 C 0.0688(5) 0.3189(4) 0.2901(2) 0.0623(7) Uani 1 1 d . . . . .
H6 H 0.194309 0.383474 0.285251 0.075 Uiso 1 1 calc R U . . .
C7 C 0.2558(5) 0.2513(3) 0.44819(19) 0.0533(6) Uani 1 1 d . . . . .
C8 C 0.4347(4) 0.1940(3) 0.60078(17) 0.0499(6) Uani 1 1 d . . . . .
C9 C 0.3936(5) 0.1210(3) 0.68077(18) 0.0556(6) Uani 1 1 d . . . . .
H9 H 0.256963 0.064641 0.680467 0.067 Uiso 1 1 calc R U . . .
C10 C 0.5525(4) 0.1306(3) 0.76123(18) 0.0555(6) Uani 1 1 d . . . . .
H10 H 0.519496 0.082321 0.814618 0.067 Uiso 1 1 calc R U . . .
C11 C 0.7600(4) 0.2110(3) 0.76375(17) 0.0508(6) Uani 1 1 d . . . . .
C12 C 0.8005(5) 0.2842(3) 0.68249(19) 0.0581(7) Uani 1 1 d . . . . .
H12 H 0.937537 0.340112 0.682613 0.070 Uiso 1 1 calc R U . . .
C13 C 0.6423(5) 0.2756(3) 0.6023(2) 0.0605(7) Uani 1 1 d . . . . .
H13 H 0.674052 0.324505 0.548922 0.073 Uiso 1 1 calc R U . . .
C14 C 0.9394(4) 0.2146(4) 0.85041(18) 0.0578(7) Uani 1 1 d . . . . .
H14A H 1.091550 0.234803 0.832184 0.069 Uiso 1 1 calc R U . . .
H14B H 0.946272 0.113858 0.878201 0.069 Uiso 1 1 calc R U . . .
C15 C 0.8994(4) 0.3298(3) 0.92415(18) 0.0490(6) Uani 1 1 d . . . . .
C16 C 0.8919(5) 0.4945(3) 0.8933(2) 0.0594(7) Uani 1 1 d . . . . .
H16A H 1.045206 0.541419 0.907671 0.071 Uiso 1 1 calc R U . . .
H16B H 0.840095 0.502336 0.827080 0.071 Uiso 1 1 calc R U . . .
C17 C 0.5909(4) 0.4571(3) 0.97476(17) 0.0523(6) Uani 1 1 d . . . . .
N1 N 0.2604(4) 0.1741(3) 0.52236(15) 0.0540(5) Uani 1 1 d . . . . .
N2 N 0.6716(4) 0.3196(3) 0.95572(14) 0.0498(5) Uani 1 1 d . . . . .
O2 O 0.7258(3) 0.5667(2) 0.94476(14) 0.0633(5) Uani 1 1 d . . . . .
O1 O -0.1318(4) 0.0476(3) 0.45115(15) 0.0813(7) Uani 1 1 d . . . . .
O3 O 0.4229(3) 0.4895(3) 1.01218(14) 0.0757(7) 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 1.393(4) . ?
C1 C2 1.403(4) . ?
C1 C7 1.454(3) . ?
C2 O1 1.348(3) . ?
C2 C3 1.394(4) . ?
C3 C4 1.365(5) . ?
C4 C5 1.380(4) . ?
C5 C6 1.377(4) . ?
C7 N1 1.273(3) . ?
C8 C9 1.381(4) . ?
C8 C13 1.393(4) . ?
C8 N1 1.418(3) . ?
C9 C10 1.381(4) . ?
C10 C11 1.385(4) . ?
C11 C12 1.397(4) . ?
C11 C14 1.512(3) . ?
C12 C13 1.376(4) . ?
C14 C15 1.517(4) . ?
C15 N2 1.458(3) . ?
C15 C16 1.511(4) . ?
C16 O2 1.447(3) . ?
C17 O3 1.214(3) . ?
C17 N2 1.336(3) . ?
C17 O2 1.349(3) . ?

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 118.3(2) . . ?
C6 C1 C7 120.3(2) . . ?
C2 C1 C7 121.4(2) . . ?
O1 C2 C3 118.9(3) . . ?
O1 C2 C1 121.5(2) . . ?
C3 C2 C1 119.5(3) . . ?
C4 C3 C2 120.8(3) . . ?
C3 C4 C5 120.4(3) . . ?
C6 C5 C4 119.6(3) . . ?
C5 C6 C1 121.4(3) . . ?
N1 C7 C1 121.6(3) . . ?
C9 C8 C13 118.6(2) . . ?
C9 C8 N1 115.8(2) . . ?
C13 C8 N1 125.6(2) . . ?
C8 C9 C10 121.0(2) . . ?
C9 C10 C11 121.1(2) . . ?
C10 C11 C12 117.6(2) . . ?
C10 C11 C14 121.1(2) . . ?
C12 C11 C14 121.3(2) . . ?
C13 C12 C11 121.5(3) . . ?
C12 C13 C8 120.2(3) . . ?
C11 C14 C15 116.7(2) . . ?
N2 C15 C16 99.5(2) . . ?
N2 C15 C14 114.9(2) . . ?
C16 C15 C14 115.2(2) . . ?
O2 C16 C15 104.8(2) . . ?
O3 C17 N2 129.1(3) . . ?
O3 C17 O2 121.1(3) . . ?
N2 C17 O2 109.9(2) . . ?
C7 N1 C8 122.9(2) . . ?
C17 N2 C15 111.6(2) . . ?
C17 O2 C16 108.3(2) . . ?

_refine_diff_density_max         0.100
_refine_diff_density_min         -0.126
_refine_diff_density_rms         0.030



####################################################################### 
# 
# 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_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1983771'
loop_
_audit_author_name
_audit_author_address
'Rekha Kumari'
;ICER SSCU IISc Bangalore Karnataka
India
;
_audit_update_record             
;
2023-11-04 deposited with the CCDC.	2024-02-26 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            'C17.09 H15 N1.91 O2'
_chemical_formula_weight         279.13

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                   5.9424(3)
_cell_length_b                   8.5540(4)
_cell_length_c                   14.3274(7)
_cell_angle_alpha                90
_cell_angle_beta                 98.358(4)
_cell_angle_gamma                90
_cell_volume                     720.55(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4259
_cell_measurement_theta_min      3.9250
_cell_measurement_theta_max      27.2930

_exptl_crystal_description       Block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.287
_exptl_crystal_F_000             294
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.086
_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      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Xcalibur, Eos, Nova'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10688
_diffrn_reflns_av_unetI/netI     0.0302
_diffrn_reflns_av_R_equivalents  0.0296
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.465
_diffrn_reflns_theta_max         27.481
_diffrn_reflns_theta_full        25.242
_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 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3302
_reflns_number_gt                2626
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.874
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_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)+(0.0458P)²+0.0505P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 957 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   1.1(7)
_chemical_absolute_configuration unknown
_refine_ls_number_reflns         3302
_refine_ls_number_parameters     208
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0586
_refine_ls_R_factor_gt           0.0465
_refine_ls_wR_factor_ref         0.1128
_refine_ls_wR_factor_gt          0.1033
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.067
_refine_ls_shift/su_max          0.049
_refine_ls_shift/su_mean         0.004

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
H2A H 0.376(5) 0.113(5) 0.522(2) 0.069(10) Uiso 1 1 d . . . . .
H15 H -0.026(5) 0.034(3) 0.5195(17) 0.047(7) Uiso 1 1 d . . . . .
C1 C 1.0068(5) 0.1482(4) 1.1014(2) 0.0628(8) Uani 1 1 d . . . . .
C2 C 0.9492(6) 0.0538(4) 1.1726(3) 0.0741(9) Uani 1 1 d . . . . .
H2 H 0.811504 0.000262 1.164192 0.089 Uiso 1 1 calc R U . A 2
C3 C 1.0973(7) 0.0386(4) 1.2572(2) 0.0819(10) Uani 1 1 d . . . . .
H3 H 1.059057 -0.025434 1.305006 0.098 Uiso 1 1 calc R U . . .
C4 C 1.3003(6) 0.1189(5) 1.2695(2) 0.0721(9) Uani 1 1 d . . . . .
H4 H 1.400877 0.108915 1.325285 0.087 Uiso 1 1 calc R U . . .
C5 C 1.3523(6) 0.2135(5) 1.1987(3) 0.0762(9) Uani 1 1 d . . . . .
H5 H 1.487648 0.269756 1.206945 0.091 Uiso 1 1 calc R U . . .
C6 C 1.2070(6) 0.2258(5) 1.1164(2) 0.0748(9) Uani 1 1 d . . . . .
H6 H 1.246838 0.289722 1.068874 0.090 Uiso 1 1 calc R U . . .
N1A N 0.6747(5) 0.0998(4) 0.9910(2) 0.0652(12) Uani 0.910(10) 1 d . . P B 1
C7A C 0.8564(9) 0.1711(4) 1.0089(3) 0.0618(16) Uani 0.910(16) 1 d . . P B 1
C7B C 0.759(4) 0.092(3) 1.055(2) 0.036(9) Uiso 0.090(10) 1 d . . P B 2
N1B C 0.742(7) 0.180(4) 0.971(3) 0.035(11) Uiso 0.090(16) 1 d . . P B 2
C8 C 0.5311(5) 0.1223(4) 0.9035(2) 0.0585(7) Uani 1 1 d . . . . .
C9 C 0.5780(5) 0.2094(4) 0.8268(2) 0.0682(9) Uani 1 1 d . . . . .
H9 H 0.714589 0.263679 0.830601 0.082 Uiso 1 1 calc R U . . .
C10 C 0.4245(5) 0.2162(4) 0.7453(2) 0.0616(8) Uani 1 1 d . . . . .
H10 H 0.458938 0.275726 0.694964 0.074 Uiso 1 1 calc R U . . .
C11 C 0.2194(4) 0.1363(3) 0.73636(19) 0.0517(6) Uani 1 1 d . . . . .
C12 C 0.1728(5) 0.0519(4) 0.8138(2) 0.0626(8) Uani 1 1 d . . . . .
H12 H 0.034923 -0.000740 0.810677 0.075 Uiso 1 1 calc R U . . .
C13 C 0.3259(5) 0.0444(4) 0.8950(2) 0.0651(8) Uani 1 1 d . . . . .
H13 H 0.290726 -0.014529 0.945489 0.078 Uiso 1 1 calc R U . . .
C14 C 0.0549(5) 0.1399(4) 0.6460(2) 0.0569(7) Uani 1 1 d . . . . .
H14A H 0.060700 0.243039 0.618263 0.068 Uiso 1 1 calc R U . . .
H14B H -0.097463 0.125414 0.661295 0.068 Uiso 1 1 calc R U . . .
C15 C 0.0941(4) 0.0195(3) 0.57217(19) 0.0495(6) Uani 1 1 d . . . . .
C16 C 0.0995(5) -0.1500(4) 0.6039(2) 0.0587(7) Uani 1 1 d . . . . .
H16A H 0.137564 -0.157138 0.671980 0.070 Uiso 1 1 calc R U . . .
H16B H -0.046926 -0.199395 0.585018 0.070 Uiso 1 1 calc R U . . .
C17 C 0.4033(4) -0.1107(3) 0.52796(19) 0.0527(7) Uani 1 1 d . . . . .
N2 N 0.3176(4) 0.0292(3) 0.54198(16) 0.0522(6) Uani 1 1 d . . . . .
O1 O 0.2719(3) -0.2231(2) 0.55827(15) 0.0639(6) Uani 1 1 d . . . . .
O2 O 0.5721(4) -0.1440(3) 0.49348(17) 0.0763(7) 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 1.352(5) . ?
C1 C2 1.384(5) . ?
C1 C7A 1.500(6) . ?
C1 C7B 1.60(3) . ?
C2 C3 1.396(5) . ?
C2 C7B 1.92(3) . ?
C3 C4 1.377(5) . ?
C4 C5 1.367(5) . ?
C5 C6 1.361(4) . ?
N1A C7A 1.234(6) . ?
N1A C8 1.423(4) . ?
C7B N1B 1.41(5) . ?
N1B C8 1.55(4) . ?
C8 C13 1.380(4) . ?
C8 C9 1.389(4) . ?
C9 C10 1.374(4) . ?
C10 C11 1.386(4) . ?
C11 C12 1.386(4) . ?
C11 C14 1.505(4) . ?
C12 C13 1.370(4) . ?
C14 C15 1.518(4) . ?
C15 N2 1.457(3) . ?
C15 C16 1.519(4) . ?
C16 O1 1.436(3) . ?
C17 O2 1.215(3) . ?
C17 N2 1.327(4) . ?
C17 O1 1.350(3) . ?

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 118.4(3) . . ?
C6 C1 C7A 118.3(3) . . ?
C2 C1 C7A 123.3(3) . . ?
C6 C1 C7B 161.8(11) . . ?
C2 C1 C7B 79.6(11) . . ?
C1 C2 C3 120.2(3) . . ?
C1 C2 C7B 55.2(8) . . ?
C3 C2 C7B 175.0(9) . . ?
C4 C3 C2 119.6(3) . . ?
C5 C4 C3 119.3(3) . . ?
C6 C5 C4 120.4(3) . . ?
C1 C6 C5 122.2(3) . . ?
C7A N1A C8 120.7(3) . . ?
N1A C7A C1 120.7(4) . . ?
N1B C7B C1 98(2) . . ?
N1B C7B C2 143(2) . . ?
C1 C7B C2 45.3(8) . . ?
C7B N1B C8 108(2) . . ?
C13 C8 C9 117.7(3) . . ?
C13 C8 N1A 114.9(3) . . ?
C9 C8 N1A 127.3(3) . . ?
C13 C8 N1B 146.6(13) . . ?
C9 C8 N1B 94.9(13) . . ?
C10 C9 C8 120.7(3) . . ?
C9 C10 C11 121.6(3) . . ?
C12 C11 C10 117.3(3) . . ?
C12 C11 C14 121.3(3) . . ?
C10 C11 C14 121.4(3) . . ?
C13 C12 C11 121.3(3) . . ?
C12 C13 C8 121.5(3) . . ?
C11 C14 C15 116.0(2) . . ?
N2 C15 C14 114.0(2) . . ?
N2 C15 C16 99.4(2) . . ?
C14 C15 C16 116.0(2) . . ?
O1 C16 C15 105.3(2) . . ?
O2 C17 N2 129.1(3) . . ?
O2 C17 O1 121.0(3) . . ?
N2 C17 O1 109.9(2) . . ?
C17 N2 C15 112.3(2) . . ?
C17 O1 C16 108.7(2) . . ?

_refine_diff_density_max         0.204
_refine_diff_density_min         -0.148
_refine_diff_density_rms         0.030



####################################################################### 
# 
# 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_shelx_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1983772'
loop_
_audit_author_name
_audit_author_address
'Rekha Kumari'
;ICER SSCU IISc Bangalore Karnataka
India
;
_audit_update_record             
;
2023-11-04 deposited with the CCDC.	2024-02-26 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            'C17 H16 N2 O2'
_chemical_formula_weight         280.32

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                   5.90090(10)
_cell_length_b                   8.4145(2)
_cell_length_c                   14.2428(3)
_cell_angle_alpha                90
_cell_angle_beta                 98.443(2)
_cell_angle_gamma                90
_cell_volume                     699.54(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6165
_cell_measurement_theta_min      3.9590
_cell_measurement_theta_max      27.3560

_exptl_crystal_description       Block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.331
_exptl_crystal_F_000             296
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.089
_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      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Xcalibur, Eos, Nova'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10790
_diffrn_reflns_av_unetI/netI     0.0339
_diffrn_reflns_av_R_equivalents  0.0326
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.490
_diffrn_reflns_theta_max         27.480
_diffrn_reflns_theta_full        25.000
_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 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3211
_reflns_number_gt                3033
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.873
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_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)+(0.0379P)²+0.1104P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1253 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   1.2(6)
_chemical_absolute_configuration unknown
_refine_ls_number_reflns         3211
_refine_ls_number_parameters     202
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0398
_refine_ls_R_factor_gt           0.0368
_refine_ls_wR_factor_ref         0.0856
_refine_ls_wR_factor_gt          0.0825
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_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
H2A H 0.133(4) 0.140(4) 0.4790(17) 0.029(7) Uiso 1 1 d . . . . .
H7 H -0.408(4) 0.272(3) 0.0347(18) 0.027(7) Uiso 1 1 d . . . . .
H15 H 0.542(4) 0.051(3) 0.4832(15) 0.014(5) Uiso 1 1 d . . . . .
C1 C -0.5103(3) 0.1752(2) -0.09796(15) 0.0194(4) Uani 1 1 d . . . . .
C2 C -0.4492(4) 0.0771(3) -0.16961(15) 0.0220(5) Uani 1 1 d . . . . .
H2 H -0.309714 0.023722 -0.160413 0.026 Uiso 1 1 calc R U . . .
C3 C -0.5962(4) 0.0595(3) -0.25412(16) 0.0252(5) Uani 1 1 d . . . . .
H3 H -0.554724 -0.005568 -0.301546 0.030 Uiso 1 1 calc R U . . .
C4 C -0.8063(4) 0.1388(3) -0.26869(16) 0.0241(5) Uani 1 1 d . . . . .
H4 H -0.904643 0.126266 -0.325517 0.029 Uiso 1 1 calc R U . . .
C5 C -0.8677(4) 0.2360(3) -0.19830(16) 0.0248(5) Uani 1 1 d . . . . .
H5 H -1.007129 0.289491 -0.207942 0.030 Uiso 1 1 calc R U . . .
C6 C -0.7211(4) 0.2541(3) -0.11304(16) 0.0232(5) Uani 1 1 d . . . . .
H6 H -0.763654 0.319057 -0.065765 0.028 Uiso 1 1 calc R U . . .
C7 C -0.3572(4) 0.1981(3) -0.00781(16) 0.0211(5) Uani 1 1 d . . . . .
C8 C -0.0206(3) 0.1451(3) 0.09786(14) 0.0194(4) Uani 1 1 d . . . . .
C9 C 0.1890(4) 0.0666(3) 0.10514(15) 0.0207(4) Uani 1 1 d . . . . .
H9 H 0.224310 0.007556 0.054018 0.025 Uiso 1 1 calc R U . . .
C10 C 0.3458(4) 0.0754(3) 0.18779(15) 0.0217(5) Uani 1 1 d . . . . .
H10 H 0.485710 0.023301 0.190988 0.026 Uiso 1 1 calc R U . . .
C11 C 0.2964(3) 0.1610(3) 0.26604(14) 0.0181(4) Uani 1 1 d . . . . .
C12 C 0.0875(4) 0.2416(3) 0.25811(15) 0.0220(5) Uani 1 1 d . . . . .
H12 H 0.052893 0.301175 0.309133 0.026 Uiso 1 1 calc R U . . .
C13 C -0.0694(4) 0.2343(3) 0.17538(16) 0.0235(5) Uani 1 1 d . . . . .
H13 H -0.207475 0.288878 0.171494 0.028 Uiso 1 1 calc R U . . .
C14 C 0.4623(3) 0.1638(3) 0.35805(15) 0.0196(4) Uani 1 1 d . . . . .
H14A H 0.455225 0.267593 0.387051 0.024 Uiso 1 1 calc R U . . .
H14B H 0.616491 0.149789 0.343355 0.024 Uiso 1 1 calc R U . . .
C15 C 0.4180(3) 0.0369(3) 0.43043(14) 0.0175(4) Uani 1 1 d . . . . .
C16 C 0.4079(3) -0.1353(3) 0.39445(14) 0.0200(4) Uani 1 1 d . . . . .
H16A H 0.369628 -0.138640 0.325878 0.024 Uiso 1 1 calc R U . . .
H16B H 0.553660 -0.188370 0.412743 0.024 Uiso 1 1 calc R U . . .
C17 C 0.1004(3) -0.0942(3) 0.47172(14) 0.0185(4) Uani 1 1 d . . . . .
N1 N -0.1693(3) 0.1233(2) 0.01046(13) 0.0222(4) Uani 1 1 d . . . . .
N2 N 0.1916(3) 0.0488(2) 0.46016(12) 0.0189(4) Uani 1 1 d . . . . .
O1 O 0.2293(2) -0.20959(18) 0.43951(11) 0.0216(3) Uani 1 1 d . . . . .
O2 O -0.0731(2) -0.12686(19) 0.50558(11) 0.0245(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 1.398(3) . ?
C1 C2 1.400(3) . ?
C1 C7 1.470(3) . ?
C2 C3 1.384(3) . ?
C3 C4 1.396(3) . ?
C4 C5 1.383(3) . ?
C5 C6 1.392(3) . ?
C7 N1 1.269(3) . ?
C8 C9 1.393(3) . ?
C8 C13 1.399(3) . ?
C8 N1 1.426(3) . ?
C9 C10 1.388(3) . ?
C10 C11 1.394(3) . ?
C11 C12 1.397(3) . ?
C11 C14 1.517(3) . ?
C12 C13 1.389(3) . ?
C14 C15 1.533(3) . ?
C15 N2 1.463(3) . ?
C15 C16 1.535(3) . ?
C16 O1 1.453(2) . ?
C17 O2 1.225(2) . ?
C17 N2 1.338(3) . ?
C17 O1 1.354(2) . ?

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 119.1(2) . . ?
C6 C1 C7 119.37(19) . . ?
C2 C1 C7 121.52(19) . . ?
C3 C2 C1 120.1(2) . . ?
C2 C3 C4 120.5(2) . . ?
C5 C4 C3 119.8(2) . . ?
C4 C5 C6 120.1(2) . . ?
C5 C6 C1 120.5(2) . . ?
N1 C7 C1 121.4(2) . . ?
C9 C8 C13 118.61(19) . . ?
C9 C8 N1 115.44(18) . . ?
C13 C8 N1 125.93(19) . . ?
C10 C9 C8 120.79(19) . . ?
C9 C10 C11 120.94(19) . . ?
C10 C11 C12 118.16(19) . . ?
C10 C11 C14 120.97(19) . . ?
C12 C11 C14 120.85(18) . . ?
C13 C12 C11 121.17(19) . . ?
C12 C13 C8 120.30(19) . . ?
C11 C14 C15 114.73(17) . . ?
N2 C15 C14 113.59(17) . . ?
N2 C15 C16 99.72(16) . . ?
C14 C15 C16 115.78(17) . . ?
O1 C16 C15 104.69(16) . . ?
O2 C17 N2 128.6(2) . . ?
O2 C17 O1 121.06(19) . . ?
N2 C17 O1 110.30(17) . . ?
C7 N1 C8 121.48(18) . . ?
C17 N2 C15 112.03(18) . . ?
C17 O1 C16 108.73(15) . . ?

_refine_diff_density_max         0.199
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.039



####################################################################### 
# 
# 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_shelx_CCDC3
_database_code_depnum_ccdc_archive 'CCDC 1972047'
loop_
_audit_author_name
_audit_author_address
'Rekha Kumari'
;ICER SSCU IISc Bangalore Karnataka
India
;
_audit_update_record             
;
2023-11-04 deposited with the CCDC.	2024-02-26 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            'C17 H16 N2 O3'
_chemical_formula_weight         296.32

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                   5.71660(10)
_cell_length_b                   8.7186(2)
_cell_length_c                   14.3362(3)
_cell_angle_alpha                90
_cell_angle_beta                 97.672(2)
_cell_angle_gamma                90
_cell_volume                     708.13(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    7304
_cell_measurement_theta_min      4.0430
_cell_measurement_theta_max      27.4170

_exptl_crystal_description       Plate
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.390
_exptl_crystal_F_000             312
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.097
_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      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Xcalibur, Eos, Nova'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10961
_diffrn_reflns_av_unetI/netI     0.0289
_diffrn_reflns_av_R_equivalents  0.0285
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.596
_diffrn_reflns_theta_max         27.462
_diffrn_reflns_theta_full        2.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.000
_reflns_number_total             3247
_reflns_number_gt                3129
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.877
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    0.000

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_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)+(0.0349P)²+0.1140P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1383 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   1.1(4)
_chemical_absolute_configuration unknown
_refine_ls_number_reflns         3247
_refine_ls_number_parameters     207
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0330
_refine_ls_R_factor_gt           0.0316
_refine_ls_wR_factor_ref         0.0751
_refine_ls_wR_factor_gt          0.0737
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_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
H1 H 0.499(6) 0.981(4) 1.010(2) 0.057(9) Uiso 1 1 d . . . . .
H2A H -0.114(4) 0.800(3) 0.5297(16) 0.023(6) Uiso 1 1 d . . . . .
C1 C 0.4407(3) 0.8095(2) 1.13368(13) 0.0184(4) Uani 1 1 d . . . . .
C2 C 0.6280(3) 0.9130(2) 1.12618(13) 0.0204(4) Uani 1 1 d . . . . .
C3 C 0.8175(3) 0.9210(2) 1.19853(14) 0.0246(4) Uani 1 1 d . . . . .
H3 H 0.941952 0.987884 1.193498 0.030 Uiso 1 1 calc R U . . .
C4 C 0.8203(3) 0.8297(2) 1.27763(14) 0.0235(4) Uani 1 1 d . . . . .
H4 H 0.948005 0.834573 1.325089 0.028 Uiso 1 1 calc R U . . .
C5 C 0.6339(4) 0.7305(2) 1.28686(15) 0.0237(4) Uani 1 1 d . . . . .
H5 H 0.635574 0.670823 1.340727 0.028 Uiso 1 1 calc R U . . .
C6 C 0.4467(4) 0.7212(2) 1.21563(14) 0.0224(4) Uani 1 1 d . . . . .
H6 H 0.322202 0.655125 1.222113 0.027 Uiso 1 1 calc R U . . .
C7 C 0.2478(3) 0.7903(2) 1.05730(13) 0.0188(4) Uani 1 1 d . . . . .
H7 H 0.130225 0.718500 1.063049 0.023 Uiso 1 1 calc R U . . .
C8 C 0.0613(3) 0.8500(2) 0.90392(13) 0.0187(4) Uani 1 1 d . . . . .
C9 C 0.1042(3) 0.9219(2) 0.82117(13) 0.0204(4) Uani 1 1 d . . . . .
H9 H 0.242834 0.977345 0.820289 0.024 Uiso 1 1 calc R U . . .
C10 C -0.0568(3) 0.9118(2) 0.74007(13) 0.0197(4) Uani 1 1 d . . . . .
H10 H -0.024278 0.959581 0.685234 0.024 Uiso 1 1 calc R U . . .
C11 C -0.2677(3) 0.8306(2) 0.73995(13) 0.0188(4) Uani 1 1 d . . . . .
C12 C -0.3095(3) 0.7594(2) 0.82340(14) 0.0201(4) Uani 1 1 d . . . . .
H12 H -0.448954 0.704898 0.824565 0.024 Uiso 1 1 calc R U . . .
C13 C -0.1484(3) 0.7679(2) 0.90448(14) 0.0209(4) Uani 1 1 d . . . . .
H13 H -0.179826 0.719183 0.959156 0.025 Uiso 1 1 calc R U . . .
C14 C -0.4482(3) 0.8285(2) 0.65267(13) 0.0208(4) Uani 1 1 d . . . . .
H14A H -0.453490 0.929845 0.624577 0.025 Uiso 1 1 calc R U . . .
H14B H -0.601962 0.808891 0.671759 0.025 Uiso 1 1 calc R U . . .
C15 C -0.4074(3) 0.7118(2) 0.57722(13) 0.0179(4) Uani 1 1 d . . . . .
H15 H -0.529195 0.724672 0.522834 0.022 Uiso 1 1 calc R U . . .
C16 C -0.4032(3) 0.5446(2) 0.60888(14) 0.0204(4) Uani 1 1 d . . . . .
H16A H -0.350203 0.536260 0.675843 0.024 Uiso 1 1 calc R U . . .
H16B H -0.558581 0.498721 0.595301 0.024 Uiso 1 1 calc R U . . .
C17 C -0.0958(3) 0.5817(2) 0.52520(12) 0.0185(4) Uani 1 1 d . . . . .
N1 N 0.2382(3) 0.87114(18) 0.98234(11) 0.0193(3) Uani 1 1 d . . . . .
N2 N -0.1744(3) 0.72044(19) 0.54575(11) 0.0177(3) Uani 1 1 d . . . . .
O1 O 0.6306(3) 1.00306(17) 1.04996(10) 0.0267(3) Uani 1 1 d . . . . .
O2 O -0.2373(2) 0.47117(15) 0.55466(10) 0.0220(3) Uani 1 1 d . . . . .
O3 O 0.0740(2) 0.54692(17) 0.48675(10) 0.0255(3) 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 1.401(3) . ?
C1 C2 1.415(3) . ?
C1 C7 1.456(3) . ?
C2 O1 1.347(2) . ?
C2 C3 1.398(3) . ?
C3 C4 1.384(3) . ?
C4 C5 1.392(3) . ?
C5 C6 1.379(3) . ?
C7 N1 1.280(2) . ?
C8 C9 1.392(3) . ?
C8 C13 1.398(3) . ?
C8 N1 1.420(2) . ?
C9 C10 1.386(3) . ?
C10 C11 1.398(3) . ?
C11 C12 1.396(3) . ?
C11 C14 1.512(3) . ?
C12 C13 1.385(3) . ?
C14 C15 1.526(3) . ?
C15 N2 1.464(2) . ?
C15 C16 1.526(3) . ?
C16 O2 1.453(2) . ?
C17 O3 1.217(2) . ?
C17 N2 1.337(2) . ?
C17 O2 1.361(2) . ?

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 118.67(17) . . ?
C6 C1 C7 119.91(17) . . ?
C2 C1 C7 121.40(17) . . ?
O1 C2 C3 118.76(18) . . ?
O1 C2 C1 121.57(18) . . ?
C3 C2 C1 119.67(18) . . ?
C4 C3 C2 120.14(19) . . ?
C3 C4 C5 120.66(19) . . ?
C6 C5 C4 119.60(19) . . ?
C5 C6 C1 121.23(19) . . ?
N1 C7 C1 120.74(17) . . ?
C9 C8 C13 118.96(18) . . ?
C9 C8 N1 115.39(17) . . ?
C13 C8 N1 125.63(17) . . ?
C10 C9 C8 120.92(18) . . ?
C9 C10 C11 120.59(17) . . ?
C12 C11 C10 118.06(17) . . ?
C12 C11 C14 121.85(17) . . ?
C10 C11 C14 120.01(17) . . ?
C13 C12 C11 121.63(18) . . ?
C12 C13 C8 119.84(18) . . ?
C11 C14 C15 116.29(15) . . ?
N2 C15 C16 99.33(15) . . ?
N2 C15 C14 114.54(15) . . ?
C16 C15 C14 115.09(16) . . ?
O2 C16 C15 104.32(15) . . ?
O3 C17 N2 129.59(19) . . ?
O3 C17 O2 120.47(18) . . ?
N2 C17 O2 109.94(16) . . ?
C7 N1 C8 122.65(17) . . ?
C17 N2 C15 111.56(16) . . ?
C17 O2 C16 108.15(14) . . ?

_refine_diff_density_max         0.185
_refine_diff_density_min         -0.172
_refine_diff_density_rms         0.035



####################################################################### 
# 
# 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_shelx_CCDC4
_database_code_depnum_ccdc_archive 'CCDC 2305762'
loop_
_audit_author_name
_audit_author_address
'Rekha Kumari'
;ICER and Solid State and Structural Chemistry Unit IISc Bengaluru
India
;
_audit_update_record             
;
2023-11-24 deposited with the CCDC.	2024-02-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8.50 H7 N O1.50'
_chemical_formula_weight         147.15

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                   5.780(8)
_cell_length_b                   8.827(12)
_cell_length_c                   14.66(2)
_cell_angle_alpha                90
_cell_angle_beta                 98.19(4)
_cell_angle_gamma                90
_cell_volume                     740.5(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    390(2)
_cell_measurement_reflns_used    1173
_cell_measurement_theta_min      2.70
_cell_measurement_theta_max      19.68

_exptl_crystal_description       Plate
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_F_000             308
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.092
_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      390(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            7587
_diffrn_reflns_av_unetI/netI     0.1525
_diffrn_reflns_av_R_equivalents  0.1673
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.403
_diffrn_reflns_theta_max         25.061
_diffrn_reflns_theta_full        25.061
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measured_fraction_theta_full 0.955
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_Laue_measured_fraction_full 0.955
_diffrn_reflns_point_group_measured_fraction_max 0.939
_diffrn_reflns_point_group_measured_fraction_full 0.939
_reflns_number_total             2476
_reflns_number_gt                1061
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.838
_reflns_Friedel_fraction_max     0.920
_reflns_Friedel_fraction_full    0.920

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_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)+(0.2000P)²] 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 252 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -3.9(10)
_chemical_absolute_configuration Unknown
_refine_ls_number_reflns         2476
_refine_ls_number_parameters     199
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.2716
_refine_ls_R_factor_gt           0.1288
_refine_ls_wR_factor_ref         0.4538
_refine_ls_wR_factor_gt          0.3079
_refine_ls_goodness_of_fit_ref   1.287
_refine_ls_restrained_S_all      1.286
_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 0.072(3) 0.4298(15) 0.3731(13) 0.078(5) Uani 1 1 d . . . . .
C2 C -0.115(3) 0.318(2) 0.3777(12) 0.080(4) Uani 1 1 d . . . . .
C3 C -0.293(3) 0.312(3) 0.3025(12) 0.102(6) Uani 1 1 d . . . . .
H3 H -0.415427 0.243814 0.303341 0.122 Uiso 1 1 calc R U . . .
C4 C -0.288(3) 0.403(3) 0.2280(14) 0.106(7) Uani 1 1 d . . . . .
H4 H -0.412647 0.399458 0.180214 0.128 Uiso 1 1 calc R U . . .
C5 C -0.105(3) 0.502(2) 0.2206(15) 0.099(6) Uani 1 1 d . . . . .
H5 H -0.104316 0.562479 0.168685 0.118 Uiso 1 1 calc R U . . .
C6 C 0.069(3) 0.5077(18) 0.2907(11) 0.078(4) Uani 1 1 d . . . . .
H6 H 0.197969 0.567834 0.283904 0.094 Uiso 1 1 calc R U . . .
C7 C 0.256(3) 0.439(2) 0.4527(11) 0.076(4) Uani 1 1 d . . . . .
H7 H 0.381667 0.502900 0.448051 0.091 Uiso 1 1 calc R U . . .
C8 C 0.432(2) 0.3836(17) 0.6003(11) 0.073(4) Uani 1 1 d . . . . .
C9 C 0.395(3) 0.3080(19) 0.6805(10) 0.073(4) Uani 1 1 d . . . . .
H9 H 0.258532 0.251445 0.679351 0.088 Uiso 1 1 calc R U . . .
C10 C 0.554(3) 0.313(2) 0.7636(13) 0.086(5) Uani 1 1 d . . . . .
H10 H 0.525509 0.259326 0.815538 0.103 Uiso 1 1 calc R U . . .
C11 C 0.755(2) 0.4015(19) 0.7640(10) 0.075(4) Uani 1 1 d . . . . .
C12 C 0.793(3) 0.476(2) 0.6855(10) 0.072(4) Uani 1 1 d . . . . .
H12 H 0.929136 0.533502 0.687374 0.086 Uiso 1 1 calc R U . . .
C13 C 0.639(3) 0.4716(18) 0.6030(12) 0.081(5) Uani 1 1 d . . . . .
H13 H 0.670916 0.524294 0.551275 0.097 Uiso 1 1 calc R U . . .
C14 C 0.932(3) 0.403(2) 0.8520(10) 0.085(5) Uani 1 1 d . . . . .
H14A H 0.932149 0.304120 0.880434 0.101 Uiso 1 1 calc R U . . .
H14B H 1.086441 0.418818 0.834624 0.101 Uiso 1 1 calc R U . . .
C15 C 0.897(3) 0.5156(17) 0.9203(13) 0.078(4) Uani 1 1 d . . . . .
H15 H 1.020639 0.503122 0.972895 0.094 Uiso 1 1 calc R U . . .
C16 C 0.881(3) 0.686(2) 0.8950(15) 0.093(6) Uani 1 1 d . . . . .
H16A H 1.032524 0.734115 0.910697 0.112 Uiso 1 1 calc R U . . .
H16B H 0.831035 0.698569 0.829414 0.112 Uiso 1 1 calc R U . . .
C17 C 0.587(3) 0.649(2) 0.9758(15) 0.092(6) Uani 1 1 d . . . . .
N1 N 0.259(2) 0.3705(15) 0.5225(8) 0.072(3) Uani 1 1 d . . . . .
N2 N 0.665(2) 0.5065(14) 0.9558(12) 0.086(4) Uani 1 1 d . . . . .
H2 H 0.590422 0.423744 0.962534 0.103 Uiso 1 1 calc R U . . .
O1 O -0.131(3) 0.245(2) 0.4527(10) 0.126(6) Uani 1 1 d . . . . .
H1 H -0.011709 0.258174 0.489532 0.189 Uiso 1 1 calc R U . . .
O2 O 0.720(2) 0.7511(13) 0.9448(10) 0.098(4) Uani 1 1 d . . . . .
O3 O 0.418(2) 0.6687(16) 1.0110(11) 0.112(5) 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 1.39(2) . ?
C1 C7 1.47(2) . ?
C1 C2 1.47(2) . ?
C2 O1 1.29(2) . ?
C2 C3 1.40(2) . ?
C3 C4 1.36(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.39(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.34(2) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 N1 1.19(2) . ?
C7 H7 0.9300 . ?
C8 C9 1.40(2) . ?
C8 N1 1.412(19) . ?
C8 C13 1.42(2) . ?
C9 C10 1.42(2) . ?
C9 H9 0.9300 . ?
C10 C11 1.40(2) . ?
C10 H10 0.9300 . ?
C11 C12 1.37(2) . ?
C11 C14 1.531(18) . ?
C12 C13 1.40(2) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 C15 1.44(2) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 N2 1.51(2) . ?
C15 C16 1.55(2) . ?
C15 H15 0.9800 . ?
C16 O2 1.39(2) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 O3 1.183(19) . ?
C17 O2 1.30(2) . ?
C17 N2 1.38(2) . ?
N2 H2 0.8600 . ?
O1 H1 0.8200 . ?

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 C7 125.6(15) . . ?
C6 C1 C2 117.1(14) . . ?
C7 C1 C2 117.0(16) . . ?
O1 C2 C3 121.2(15) . . ?
O1 C2 C1 121.1(15) . . ?
C3 C2 C1 117.0(16) . . ?
C4 C3 C2 120.8(17) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C3 C4 C5 122.5(15) . . ?
C3 C4 H4 118.8 . . ?
C5 C4 H4 118.8 . . ?
C6 C5 C4 117.7(19) . . ?
C6 C5 H5 121.1 . . ?
C4 C5 H5 121.1 . . ?
C5 C6 C1 124.4(17) . . ?
C5 C6 H6 117.8 . . ?
C1 C6 H6 117.8 . . ?
N1 C7 C1 125.3(16) . . ?
N1 C7 H7 117.4 . . ?
C1 C7 H7 117.4 . . ?
C9 C8 N1 117.6(13) . . ?
C9 C8 C13 118.0(14) . . ?
N1 C8 C13 124.4(14) . . ?
C8 C9 C10 123.4(15) . . ?
C8 C9 H9 118.3 . . ?
C10 C9 H9 118.3 . . ?
C11 C10 C9 117.1(16) . . ?
C11 C10 H10 121.4 . . ?
C9 C10 H10 121.4 . . ?
C12 C11 C10 120.0(14) . . ?
C12 C11 C14 122.1(15) . . ?
C10 C11 C14 117.8(16) . . ?
C11 C12 C13 123.4(14) . . ?
C11 C12 H12 118.3 . . ?
C13 C12 H12 118.3 . . ?
C12 C13 C8 118.1(14) . . ?
C12 C13 H13 120.9 . . ?
C8 C13 H13 120.9 . . ?
C15 C14 C11 116.6(13) . . ?
C15 C14 H14A 108.2 . . ?
C11 C14 H14A 108.2 . . ?
C15 C14 H14B 108.2 . . ?
C11 C14 H14B 108.2 . . ?
H14A C14 H14B 107.3 . . ?
C14 C15 N2 115.1(14) . . ?
C14 C15 C16 120.6(18) . . ?
N2 C15 C16 96.3(12) . . ?
C14 C15 H15 108.0 . . ?
N2 C15 H15 108.0 . . ?
C16 C15 H15 108.0 . . ?
O2 C16 C15 107.2(14) . . ?
O2 C16 H16A 110.3 . . ?
C15 C16 H16A 110.3 . . ?
O2 C16 H16B 110.3 . . ?
C15 C16 H16B 110.3 . . ?
H16A C16 H16B 108.5 . . ?
O3 C17 O2 128.1(17) . . ?
O3 C17 N2 122(2) . . ?
O2 C17 N2 109.3(17) . . ?
C7 N1 C8 125.0(14) . . ?
C17 N2 C15 110.8(14) . . ?
C17 N2 H2 124.6 . . ?
C15 N2 H2 124.6 . . ?
C2 O1 H1 109.5 . . ?
C17 O2 C16 111.8(13) . . ?

_refine_diff_density_max         0.478
_refine_diff_density_min         -0.446
_refine_diff_density_rms         0.123



####################################################################### 
# 
# 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_shelx_CCDC5
_database_code_depnum_ccdc_archive 'CCDC 2026778'
loop_
_audit_author_name
_audit_author_address
'Rekha Kumari'
;ICER and Solid State and Structural Chemistry Unit IISc Bengaluru
India
;
_audit_update_record             
;
2023-11-24 deposited with the CCDC.	2024-02-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H16 N2 O2'
_chemical_formula_weight         280.32

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                   5.9304(7)
_cell_length_b                   8.5884(10)
_cell_length_c                   14.3122(18)
_cell_angle_alpha                90
_cell_angle_beta                 98.211(5)
_cell_angle_gamma                90
_cell_volume                     721.49(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2535
_cell_measurement_theta_min      2.37
_cell_measurement_theta_max      19.94

_exptl_crystal_description       Block
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.290
_exptl_crystal_F_000             296
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.086
_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      296(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            12358
_diffrn_reflns_av_unetI/netI     0.0319
_diffrn_reflns_av_R_equivalents  0.0371
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.438
_diffrn_reflns_theta_max         25.075
_diffrn_reflns_theta_full        25.075
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             2548
_reflns_number_gt                1683
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.857
_reflns_Friedel_fraction_max     0.989
_reflns_Friedel_fraction_full    0.989

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_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)+(0.0597P)²+0.1098P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 587 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.2(8)
_chemical_absolute_configuration Unknown
_refine_ls_number_reflns         2548
_refine_ls_number_parameters     194
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0833
_refine_ls_R_factor_gt           0.0491
_refine_ls_wR_factor_ref         0.1382
_refine_ls_wR_factor_gt          0.1174
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.032
_refine_ls_shift/su_max          0.001
_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
H2A H 0.110(8) 0.804(7) 0.483(3) 0.094(16) Uiso 1 1 d . . . . .
C1 C -0.5026(10) 0.8254(7) -0.1041(4) 0.0863(15) Uani 1 1 d . . . . .
C2 C -0.6982(11) 0.9024(9) -0.1182(4) 0.1041(18) Uani 1 1 d . . . . .
H2 H -0.735059 0.966850 -0.070363 0.125 Uiso 1 1 calc R U . . .
C3 C -0.8455(10) 0.8914(8) -0.1982(5) 0.1033(17) Uani 1 1 d . . . . .
H3 H -0.981225 0.947262 -0.204594 0.124 Uiso 1 1 calc R U . . .
C4 C -0.7977(10) 0.7994(8) -0.2699(4) 0.0975(16) Uani 1 1 d . . . . .
H4 H -0.899802 0.791174 -0.325411 0.117 Uiso 1 1 calc R U . . .
C5 C -0.5968(13) 0.7189(7) -0.2591(4) 0.1093(19) Uani 1 1 d . . . . .
H5 H -0.559864 0.656178 -0.307667 0.131 Uiso 1 1 calc R U . . .
C6 C -0.4475(10) 0.7314(7) -0.1748(5) 0.1058(19) Uani 1 1 d . . . . .
H6 H -0.311230 0.676220 -0.166685 0.127 Uiso 1 1 calc R U . . .
C7 C -0.3446(12) 0.8466(7) -0.0076(5) 0.105(2) Uani 1 1 d . . . . .
H7 H -0.386755 0.914103 0.037635 0.126 Uiso 1 1 calc R U . . .
C8 C -0.0363(9) 0.8032(7) 0.0973(3) 0.0791(13) Uani 1 1 d . . . . .
C9 C -0.0830(9) 0.8884(7) 0.1725(4) 0.0886(15) Uani 1 1 d . . . . .
H9 H -0.218960 0.943482 0.168743 0.106 Uiso 1 1 calc R U . . .
C10 C 0.0697(8) 0.8929(6) 0.2535(3) 0.0797(13) Uani 1 1 d . . . . .
H10 H 0.034209 0.951583 0.303980 0.096 Uiso 1 1 calc R U . . .
C11 C 0.2733(7) 0.8145(5) 0.2635(3) 0.0661(11) Uani 1 1 d . . . . .
C12 C 0.3171(8) 0.7317(6) 0.1856(4) 0.0846(15) Uani 1 1 d . . . . .
H12 H 0.454498 0.678524 0.188576 0.102 Uiso 1 1 calc R U . . .
C13 C 0.1657(9) 0.7249(7) 0.1039(3) 0.0858(14) Uani 1 1 d . . . . .
H13 H 0.200503 0.666884 0.053005 0.103 Uiso 1 1 calc R U . . .
C14 C 0.4378(8) 0.8188(6) 0.3518(3) 0.0767(13) Uani 1 1 d . . . . .
H14A H 0.433466 0.922124 0.378862 0.092 Uiso 1 1 calc R U . . .
H14B H 0.589484 0.803513 0.335535 0.092 Uiso 1 1 calc R U . . .
C15 C 0.4015(7) 0.7013(5) 0.4270(3) 0.0682(11) Uani 1 1 d . . . . .
H15 H 0.519653 0.715626 0.481631 0.082 Uiso 1 1 calc R U . . .
C16 C 0.3984(8) 0.5326(6) 0.3969(4) 0.0799(13) Uani 1 1 d . . . . .
H16A H 0.362023 0.523776 0.328832 0.096 Uiso 1 1 calc R U . . .
H16B H 0.545229 0.484211 0.416736 0.096 Uiso 1 1 calc R U . . .
C17 C 0.0944(8) 0.5716(5) 0.4724(3) 0.0703(12) Uani 1 1 d . . . . .
N1 N -0.1791(10) 0.7798(7) 0.0070(4) 0.1116(16) Uani 1 1 d . . . . .
N2 N 0.1776(6) 0.7110(5) 0.4583(2) 0.0695(10) Uani 1 1 d . . . . .
O1 O 0.2259(6) 0.4611(4) 0.4424(3) 0.0861(10) Uani 1 1 d . . . . .
O2 O -0.0737(6) 0.5384(5) 0.5074(3) 0.1010(12) 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 1.325(8) . ?
C1 C6 1.371(8) . ?
C1 C7 1.564(9) . ?
C2 C3 1.341(8) . ?
C3 C4 1.357(8) . ?
C4 C5 1.367(8) . ?
C5 C6 1.395(8) . ?
C7 N1 1.130(7) . ?
C8 C9 1.362(7) . ?
C8 C13 1.365(7) . ?
C8 N1 1.455(7) . ?
C9 C10 1.365(6) . ?
C10 C11 1.372(6) . ?
C11 C12 1.377(6) . ?
C11 C14 1.483(6) . ?
C12 C13 1.369(7) . ?
C14 C15 1.513(6) . ?
C15 N2 1.463(5) . ?
C15 C16 1.511(7) . ?
C16 O1 1.428(6) . ?
C17 O2 1.212(5) . ?
C17 N2 1.322(6) . ?
C17 O1 1.337(5) . ?

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 118.5(5) . . ?
C2 C1 C7 118.5(6) . . ?
C6 C1 C7 123.0(6) . . ?
C1 C2 C3 123.0(6) . . ?
C2 C3 C4 120.4(6) . . ?
C3 C4 C5 118.8(6) . . ?
C4 C5 C6 119.6(6) . . ?
C1 C6 C5 119.7(5) . . ?
N1 C7 C1 120.0(7) . . ?
C9 C8 C13 119.0(4) . . ?
C9 C8 N1 128.2(5) . . ?
C13 C8 N1 112.8(5) . . ?
C8 C9 C10 120.0(5) . . ?
C9 C10 C11 122.8(5) . . ?
C10 C11 C12 115.7(4) . . ?
C10 C11 C14 122.6(4) . . ?
C12 C11 C14 121.7(4) . . ?
C13 C12 C11 122.4(5) . . ?
C8 C13 C12 120.0(5) . . ?
C11 C14 C15 116.6(4) . . ?
N2 C15 C16 99.6(4) . . ?
N2 C15 C14 114.0(4) . . ?
C16 C15 C14 115.7(4) . . ?
O1 C16 C15 105.2(4) . . ?
O2 C17 N2 128.6(5) . . ?
O2 C17 O1 121.2(4) . . ?
N2 C17 O1 110.3(4) . . ?
C7 N1 C8 118.3(7) . . ?
C17 N2 C15 111.7(4) . . ?
C17 O1 C16 109.2(4) . . ?

_refine_diff_density_max         0.296
_refine_diff_density_min         -0.155
_refine_diff_density_rms         0.031



