# 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_gs_160_j_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2293003'
loop_
_audit_author_name
_audit_author_address
'Srinu Tothadi'
;CSIR CSMCRI
India
;
_audit_update_record             
;
2023-09-05 deposited with the CCDC.	2023-11-13 downloaded from the CCDC.
;
_audit_creation_date             2022-11-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H10 N2 O2'
_chemical_formula_sum            'C10 H10 N2 O2'
_chemical_formula_weight         190.20
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'

_cell_length_a                   4.8051(3)
_cell_length_b                   11.2889(8)
_cell_length_c                   16.6472(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     903.02(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5554
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      30.99
_cell_measurement_theta_min      2.18
_shelx_estimated_absorpt_T_max   0.994
_shelx_estimated_absorpt_T_min   0.974
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  0.7464
_exptl_absorpt_correction_T_min  0.6728
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1058 before and 0.0770 after correction. The Ratio of minimum to maximum transmission is 0.9014. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.399
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0846
_diffrn_reflns_av_unetI/netI     0.0223
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            43533
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.988
_diffrn_reflns_theta_max         24.987
_diffrn_reflns_theta_min         2.180
_diffrn_ambient_temperature      298
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.654
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                1300
_reflns_number_total             1599
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.129
_refine_diff_density_min         -0.170
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details 
;
 Flack x determined using 459 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.3(8)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.148
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     132
_refine_ls_number_reflns         1599
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0533
_refine_ls_R_factor_gt           0.0374
_refine_ls_restrained_S_all      1.148
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0475P)²+0.1120P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0881
_refine_ls_wR_factor_ref         0.1006
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2A), C9(H9), C10(H10)
2.c Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.9517(5) 0.23670(18) 0.41326(13) 0.0620(7) Uani 1 1 d . . . . .
O2 O 1.0658(5) 0.34953(19) 0.27273(13) 0.0634(7) Uani 1 1 d . . . . .
N1 N 0.7511(5) 0.4937(2) 0.30230(12) 0.0410(5) Uani 1 1 d . . . . .
N2 N 0.6260(5) 0.3748(2) 0.44185(14) 0.0453(6) Uani 1 1 d . . . . .
C1 C 0.1507(7) 0.6268(3) 0.4607(2) 0.0592(9) Uani 1 1 d . . . . .
H1 H 0.017606 0.655776 0.496152 0.071 Uiso 1 1 calc R . . . .
C2 C 0.2894(6) 0.5237(3) 0.47783(18) 0.0515(8) Uani 1 1 d . . . . .
H2A H 0.251034 0.482880 0.525095 0.062 Uiso 1 1 calc R . . . .
C3 C 0.4865(6) 0.4802(2) 0.42481(16) 0.0420(7) Uani 1 1 d . . . . .
C4 C 0.5492(6) 0.5405(2) 0.35420(15) 0.0381(6) Uani 1 1 d . . . . .
C5 C 0.8186(6) 0.5542(3) 0.22627(16) 0.0487(7) Uani 1 1 d . . . . .
H5A H 1.004194 0.531288 0.209397 0.058 Uiso 1 1 calc R . . . .
H5B H 0.818861 0.639125 0.235139 0.058 Uiso 1 1 calc R . . . .
C6 C 0.6147(7) 0.5250(3) 0.16020(18) 0.0606(9) Uani 1 1 d . . . . .
H6A H 0.590839 0.440682 0.157085 0.091 Uiso 1 1 calc GR . . . .
H6B H 0.684657 0.554039 0.109909 0.091 Uiso 1 1 calc GR . . . .
H6C H 0.438792 0.561671 0.171593 0.091 Uiso 1 1 calc GR . . . .
C7 C 0.8917(6) 0.3912(2) 0.31782(17) 0.0427(7) Uani 1 1 d . . . . .
C8 C 0.8258(6) 0.3280(2) 0.39609(17) 0.0439(7) Uani 1 1 d . . . . .
C9 C 0.2088(7) 0.6870(3) 0.3911(2) 0.0581(8) Uani 1 1 d . . . . .
H9 H 0.113334 0.756622 0.379503 0.070 Uiso 1 1 calc R . . . .
C10 C 0.4077(7) 0.6455(3) 0.33795(19) 0.0507(8) Uani 1 1 d . . . . .
H10 H 0.446989 0.687731 0.291344 0.061 Uiso 1 1 calc R . . . .
H2 H 0.582(6) 0.329(3) 0.4862(19) 0.060(9) Uiso 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
O1 C8 1.229(3) . ?
O2 C7 1.218(3) . ?
N1 C4 1.402(3) . ?
N1 C5 1.474(3) . ?
N1 C7 1.365(4) . ?
N2 C3 1.395(3) . ?
N2 C8 1.335(4) . ?
N2 H2 0.92(3) . ?
C1 H1 0.9300 . ?
C1 C2 1.371(4) . ?
C1 C9 1.372(5) . ?
C2 H2A 0.9300 . ?
C2 C3 1.384(4) . ?
C3 C4 1.391(4) . ?
C4 C10 1.393(4) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.510(4) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 C8 1.519(4) . ?
C9 H9 0.9300 . ?
C9 C10 1.385(4) . ?
C10 H10 0.9300 . ?

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
C4 N1 C5 120.4(2) . . ?
C7 N1 C4 123.0(2) . . ?
C7 N1 C5 116.5(2) . . ?
C3 N2 H2 121.7(19) . . ?
C8 N2 C3 124.6(2) . . ?
C8 N2 H2 113.7(19) . . ?
C2 C1 H1 120.1 . . ?
C2 C1 C9 119.9(3) . . ?
C9 C1 H1 120.1 . . ?
C1 C2 H2A 120.0 . . ?
C1 C2 C3 120.0(3) . . ?
C3 C2 H2A 120.0 . . ?
C2 C3 N2 120.1(3) . . ?
C2 C3 C4 120.9(3) . . ?
C4 C3 N2 119.0(2) . . ?
C3 C4 N1 119.1(2) . . ?
C3 C4 C10 118.3(3) . . ?
C10 C4 N1 122.6(2) . . ?
N1 C5 H5A 109.1 . . ?
N1 C5 H5B 109.1 . . ?
N1 C5 C6 112.4(2) . . ?
H5A C5 H5B 107.9 . . ?
C6 C5 H5A 109.1 . . ?
C6 C5 H5B 109.1 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
O2 C7 N1 123.4(3) . . ?
O2 C7 C8 119.4(3) . . ?
N1 C7 C8 117.2(2) . . ?
O1 C8 N2 123.6(3) . . ?
O1 C8 C7 119.4(3) . . ?
N2 C8 C7 117.0(2) . . ?
C1 C9 H9 119.6 . . ?
C1 C9 C10 120.8(3) . . ?
C10 C9 H9 119.6 . . ?
C4 C10 H10 120.0 . . ?
C9 C10 C4 120.1(3) . . ?
C9 C10 H10 120.0 . . ?

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
O2 C7 C8 O1 1.0(4) . . . . ?
O2 C7 C8 N2 -177.5(2) . . . . ?
N1 C4 C10 C9 179.5(3) . . . . ?
N1 C7 C8 O1 -178.5(3) . . . . ?
N1 C7 C8 N2 3.1(4) . . . . ?
N2 C3 C4 N1 -0.1(4) . . . . ?
N2 C3 C4 C10 179.9(2) . . . . ?
C1 C2 C3 N2 -179.4(3) . . . . ?
C1 C2 C3 C4 0.7(4) . . . . ?
C1 C9 C10 C4 0.9(5) . . . . ?
C2 C1 C9 C10 -0.5(5) . . . . ?
C2 C3 C4 N1 179.7(2) . . . . ?
C2 C3 C4 C10 -0.3(4) . . . . ?
C3 N2 C8 O1 177.9(3) . . . . ?
C3 N2 C8 C7 -3.7(4) . . . . ?
C3 C4 C10 C9 -0.5(4) . . . . ?
C4 N1 C5 C6 -82.0(3) . . . . ?
C4 N1 C7 O2 179.4(3) . . . . ?
C4 N1 C7 C8 -1.1(4) . . . . ?
C5 N1 C4 C3 178.9(2) . . . . ?
C5 N1 C4 C10 -1.1(4) . . . . ?
C5 N1 C7 O2 0.2(4) . . . . ?
C5 N1 C7 C8 179.7(2) . . . . ?
C7 N1 C4 C3 -0.3(4) . . . . ?
C7 N1 C4 C10 179.7(3) . . . . ?
C7 N1 C5 C6 97.2(3) . . . . ?
C8 N2 C3 C2 -177.5(3) . . . . ?
C8 N2 C3 C4 2.3(4) . . . . ?
C9 C1 C2 C3 -0.3(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
