# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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 2120651'
loop_
_audit_author_name
_audit_author_address
'Prof. Mahesh Hariharan'
;IISER TVM
India
;
_audit_update_record             
;
2021-11-08 deposited with the CCDC.	2022-01-27 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            'C8 H7 N O2'
_chemical_formula_weight         149.15

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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   5.862(3)
_cell_length_b                   7.712(4)
_cell_length_c                   14.907(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     674.0(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.470
_exptl_crystal_F_000             312
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.095
_exptl_crystal_size_min          0.048
_exptl_absorpt_coefficient_mu    0.107
_shelx_estimated_absorpt_T_min   0.984
_shelx_estimated_absorpt_T_max   0.995
_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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5841
_diffrn_reflns_av_unetI/netI     0.0475
_diffrn_reflns_av_R_equivalents  0.0547
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.733
_diffrn_reflns_theta_max         24.995
_diffrn_reflns_theta_full        24.995
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             1183
_reflns_number_gt                902
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.645
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_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)+(0.0503P)²+0.1300P] 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 279 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -2.3(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         1183
_refine_ls_number_parameters     102
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0689
_refine_ls_R_factor_gt           0.0471
_refine_ls_wR_factor_ref         0.1155
_refine_ls_wR_factor_gt          0.1044
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.023
_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 0.5324(6) 0.5924(5) 0.6588(2) 0.0366(9) Uani 1 1 d . . . . .
C2 C 0.7105(7) 0.6893(5) 0.6223(2) 0.0415(10) Uani 1 1 d . . . . .
C3 C 0.8870(7) 0.7447(5) 0.6744(3) 0.0437(10) Uani 1 1 d . . . . .
H3 H 1.006914 0.806996 0.649290 0.052 Uiso 1 1 calc R U . . .
C4 C 0.8855(6) 0.7064(5) 0.7669(3) 0.0415(10) Uani 1 1 d . . . . .
C5 C 0.7031(7) 0.6100(5) 0.8020(2) 0.0390(9) Uani 1 1 d . . . . .
C6 C 0.5244(7) 0.5527(5) 0.7489(3) 0.0410(10) Uani 1 1 d . . . . .
H6 H 0.403712 0.489931 0.773031 0.049 Uiso 1 1 calc R U . . .
N1 N 0.7415(7) 0.5928(5) 0.8932(2) 0.0625(12) Uani 1 1 d . . . . .
H1N H 0.653806 0.540066 0.930507 0.075 Uiso 1 1 calc R U . . .
C8 C 1.0316(7) 0.7461(6) 0.8380(3) 0.0553(12) Uani 1 1 d . . . . .
H8 H 1.165575 0.810275 0.834242 0.066 Uiso 1 1 calc R U . . .
C7 C 0.9431(9) 0.6738(6) 0.9140(3) 0.0673(15) Uani 1 1 d . . . . .
H7 H 1.008735 0.678769 0.970705 0.081 Uiso 1 1 calc R U . . .
O1 O 0.3648(5) 0.5415(4) 0.59880(18) 0.0554(9) Uani 1 1 d . . . . .
H1 H 0.272824 0.478577 0.624447 0.083 Uiso 1 1 calc R U . . .
O2 O 0.6905(5) 0.7235(4) 0.53225(16) 0.0681(11) Uani 1 1 d . . . . .
H2 H 0.808803 0.767867 0.513935 0.102 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
C1 C6 1.378(5) . ?
C1 O1 1.385(4) . ?
C1 C2 1.394(5) . ?
C2 C3 1.362(5) . ?
C2 O2 1.373(4) . ?
C3 C4 1.410(5) . ?
C3 H3 0.9300 . ?
C4 C8 1.397(5) . ?
C4 C5 1.404(5) . ?
C5 N1 1.383(5) . ?
C5 C6 1.386(5) . ?
C6 H6 0.9300 . ?
N1 C7 1.372(6) . ?
N1 H1N 0.8600 . ?
C8 C7 1.365(6) . ?
C8 H8 0.9300 . ?
C7 H7 0.9300 . ?
O1 H1 0.8200 . ?
O2 H2 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 O1 122.8(4) . . ?
C6 C1 C2 121.6(4) . . ?
O1 C1 C2 115.6(3) . . ?
C3 C2 O2 124.2(4) . . ?
C3 C2 C1 121.0(3) . . ?
O2 C2 C1 114.8(4) . . ?
C2 C3 C4 119.1(4) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 H3 120.4 . . ?
C8 C4 C5 107.4(4) . . ?
C8 C4 C3 133.8(4) . . ?
C5 C4 C3 118.7(4) . . ?
N1 C5 C6 130.9(4) . . ?
N1 C5 C4 107.1(4) . . ?
C6 C5 C4 122.1(3) . . ?
C1 C6 C5 117.4(4) . . ?
C1 C6 H6 121.3 . . ?
C5 C6 H6 121.3 . . ?
C7 N1 C5 108.6(4) . . ?
C7 N1 H1N 125.7 . . ?
C5 N1 H1N 125.7 . . ?
C7 C8 C4 107.9(4) . . ?
C7 C8 H8 126.0 . . ?
C4 C8 H8 126.0 . . ?
C8 C7 N1 109.0(4) . . ?
C8 C7 H7 125.5 . . ?
N1 C7 H7 125.5 . . ?
C1 O1 H1 109.5 . . ?
C2 O2 H2 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 1.7(6) . . . . ?
O1 C1 C2 C3 -179.0(4) . . . . ?
C6 C1 C2 O2 -177.8(4) . . . . ?
O1 C1 C2 O2 1.5(5) . . . . ?
O2 C2 C3 C4 177.9(4) . . . . ?
C1 C2 C3 C4 -1.5(6) . . . . ?
C2 C3 C4 C8 -178.1(4) . . . . ?
C2 C3 C4 C5 0.9(5) . . . . ?
C8 C4 C5 N1 -0.1(4) . . . . ?
C3 C4 C5 N1 -179.3(4) . . . . ?
C8 C4 C5 C6 178.7(4) . . . . ?
C3 C4 C5 C6 -0.5(5) . . . . ?
O1 C1 C6 C5 179.6(3) . . . . ?
C2 C1 C6 C5 -1.2(6) . . . . ?
N1 C5 C6 C1 179.1(4) . . . . ?
C4 C5 C6 C1 0.6(5) . . . . ?
C6 C5 N1 C7 -179.4(4) . . . . ?
C4 C5 N1 C7 -0.8(4) . . . . ?
C5 C4 C8 C7 0.9(5) . . . . ?
C3 C4 C8 C7 179.9(4) . . . . ?
C4 C8 C7 N1 -1.4(5) . . . . ?
C5 N1 C7 C8 1.4(5) . . . . ?

_refine_diff_density_max         0.152
_refine_diff_density_min         -0.140
_refine_diff_density_rms         0.035



_chemical_properties_physical    Air-sensitive,Moisture-sensitive
