# Supplementary Information (SI) for ChemComm.
# 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_SQIM190K_LT
_database_code_depnum_ccdc_archive 'CCDC 2383780'
loop_
_audit_author_name
_audit_author_address
'Dinabandhu Das'
;Jawaharlal Nehru University, New Delhi
India
;
_audit_update_record             
;
2024-09-13 deposited with the CCDC.	2024-11-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C4 H O4, C3 H5 N2'
_chemical_formula_sum            'C7 H6 N2 O4'
_chemical_formula_weight         182.14

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   9.4038(10)
_cell_length_b                   10.9694(13)
_cell_length_c                   7.4547(10)
_cell_angle_alpha                90
_cell_angle_beta                 100.726(4)
_cell_angle_gamma                90
_cell_volume                     755.55(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    190(2)
_cell_measurement_reflns_used    7988
_cell_measurement_theta_min      2.88
_cell_measurement_theta_max      28.38

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.601
_exptl_crystal_F_000             376
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.258
_exptl_crystal_size_mid          0.257
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.134
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.7140
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      190(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   Microfocus
_diffrn_measurement_device_type  'Bruker APEX-III CMOS detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13049
_diffrn_reflns_av_unetI/netI     0.0130
_diffrn_reflns_av_R_equivalents  0.0215
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.882
_diffrn_reflns_theta_max         28.384
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 0.980
_reflns_number_total             1861
_reflns_number_gt                1739
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    'XSEED (Barbour 2017)'
_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)+(0.0515P)²+0.1862P] 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_number_reflns         1861
_refine_ls_number_parameters     142
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0352
_refine_ls_R_factor_gt           0.0332
_refine_ls_wR_factor_ref         0.0943
_refine_ls_wR_factor_gt          0.0926
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.055
_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
O1 O 1.02342(7) 0.87795(6) 0.17771(10) 0.02489(18) Uani 1 1 d . . . . .
O3 O 0.69497(8) 0.60836(6) 0.33397(11) 0.02797(19) Uani 1 1 d . . . . .
O4 O 1.01509(8) 0.59316(6) 0.21240(11) 0.02803(19) Uani 1 1 d . . . . .
O2 O 0.70546(8) 0.90176(6) 0.29573(12) 0.0307(2) Uani 1 1 d . . . . .
C3 C 0.78226(9) 0.68204(8) 0.29110(12) 0.0195(2) Uani 1 1 d . . . . .
C2 C 0.78610(10) 0.81873(8) 0.27408(13) 0.0203(2) Uani 1 1 d . . . . .
C4 C 0.92256(9) 0.67722(8) 0.23801(12) 0.0193(2) Uani 1 1 d . . . . .
C1 C 0.93071(9) 0.80584(8) 0.22044(12) 0.0188(2) Uani 1 1 d . . . . .
N1 N 0.45553(9) 0.71003(8) 0.44097(12) 0.0249(2) Uani 1 1 d . . . . .
N2 N 0.25389(9) 0.71641(8) 0.53807(12) 0.0249(2) Uani 1 1 d . . . . .
C5 C 0.42347(11) 0.83088(9) 0.46059(14) 0.0266(2) Uani 1 1 d . . . . .
C7 C 0.35124(10) 0.64288(10) 0.48822(14) 0.0275(2) Uani 1 1 d . . . . .
C6 C 0.29650(11) 0.83498(9) 0.52193(14) 0.0267(2) Uani 1 1 d . . . . .
H5 H 0.4827(15) 0.8933(13) 0.4333(19) 0.041(4) Uiso 1 1 d . . . . .
H6 H 0.2467(15) 0.9011(13) 0.5540(18) 0.037(4) Uiso 1 1 d . . . . .
H1 H 0.5335(16) 0.6825(14) 0.401(2) 0.043(4) Uiso 1 1 d . . . . .
H7 H 0.3456(15) 0.5557(16) 0.4867(19) 0.050(4) Uiso 1 1 d . . . . .
H2 H 0.1755(17) 0.6926(15) 0.582(2) 0.045(4) Uiso 1 1 d . . . . .
H4 H 0.9926(16) 0.5152(16) 0.255(2) 0.066(5) 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 C1 1.2612(10) . ?
O3 C3 1.2356(11) . ?
O4 C4 1.3060(10) . ?
O2 C2 1.2150(11) . ?
C3 C4 1.4472(12) . ?
C3 C2 1.5057(12) . ?
C2 C1 1.4938(12) . ?
C4 C1 1.4203(12) . ?
N1 C7 1.3255(12) . ?
N1 C5 1.3734(13) . ?
N2 C7 1.3241(13) . ?
N2 C6 1.3728(13) . ?
C5 C6 1.3564(14) . ?

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
O3 C3 C4 136.90(8) . . ?
O3 C3 C2 134.48(8) . . ?
C4 C3 C2 88.62(7) . . ?
O2 C2 C1 136.75(8) . . ?
O2 C2 C3 135.22(8) . . ?
C1 C2 C3 88.03(7) . . ?
O4 C4 C1 129.72(8) . . ?
O4 C4 C3 137.04(8) . . ?
C1 C4 C3 93.24(7) . . ?
O1 C1 C4 134.27(8) . . ?
O1 C1 C2 135.62(8) . . ?
C4 C1 C2 90.11(7) . . ?
C7 N1 C5 108.67(8) . . ?
C7 N2 C6 108.92(8) . . ?
C6 C5 N1 107.00(8) . . ?
N2 C7 N1 108.69(9) . . ?
C5 C6 N2 106.72(8) . . ?

_refine_diff_density_max         0.382
_refine_diff_density_min         -0.163
_refine_diff_density_rms         0.037



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Mixture of Methanol and Water'
####################################################################### 
# 
# 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_SQIM250K_LT
_database_code_depnum_ccdc_archive 'CCDC 2383782'
loop_
_audit_author_name
_audit_author_address
'Dinabandhu Das'
;Jawaharlal Nehru University, New Delhi
India
;
_audit_update_record             
;
2024-09-13 deposited with the CCDC.	2024-11-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C4 H O4, C3 H5 N2'
_chemical_formula_sum            'C7 H6 N2 O4'
_chemical_formula_weight         182.14

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   9.4072(10)
_cell_length_b                   10.9721(13)
_cell_length_c                   7.5088(10)
_cell_angle_alpha                90
_cell_angle_beta                 100.453(4)
_cell_angle_gamma                90
_cell_volume                     762.17(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    250(2)
_cell_measurement_reflns_used    7904
_cell_measurement_theta_min      2.88
_cell_measurement_theta_max      28.38

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.587
_exptl_crystal_F_000             376
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.258
_exptl_crystal_size_mid          0.257
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.133
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.7100
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      250(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   Microfocus
_diffrn_measurement_device_type  'Bruker APEX-III CMOS detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13099
_diffrn_reflns_av_unetI/netI     0.0125
_diffrn_reflns_av_R_equivalents  0.0200
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.880
_diffrn_reflns_theta_max         28.379
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measured_fraction_theta_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_point_group_measured_fraction_full 0.979
_reflns_number_total             1876
_reflns_number_gt                1740
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_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)+(0.0629P)²+0.1293P] 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_number_reflns         1876
_refine_ls_number_parameters     142
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0378
_refine_ls_R_factor_gt           0.0356
_refine_ls_wR_factor_ref         0.1071
_refine_ls_wR_factor_gt          0.1048
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.072
_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
O1 O 1.02338(7) 0.87781(6) 0.17882(11) 0.0329(2) Uani 1 1 d . . . . .
O3 O 0.69529(8) 0.60841(7) 0.33434(12) 0.0371(2) Uani 1 1 d . . . . .
O4 O 1.01538(8) 0.59347(6) 0.21361(12) 0.0372(2) Uani 1 1 d . . . . .
O2 O 0.70548(8) 0.90145(7) 0.29612(13) 0.0410(2) Uani 1 1 d . . . . .
C3 C 0.78256(10) 0.68206(8) 0.29181(13) 0.0255(2) Uani 1 1 d . . . . .
C2 C 0.78628(10) 0.81860(8) 0.27484(13) 0.0266(2) Uani 1 1 d . . . . .
C4 C 0.92263(10) 0.67743(8) 0.23887(13) 0.0252(2) Uani 1 1 d . . . . .
C1 C 0.93082(10) 0.80579(8) 0.22138(13) 0.0247(2) Uani 1 1 d . . . . .
N1 N 0.45540(10) 0.70975(9) 0.44168(13) 0.0330(2) Uani 1 1 d . . . . .
N2 N 0.25439(9) 0.71595(9) 0.53912(13) 0.0332(2) Uani 1 1 d . . . . .
C5 C 0.42336(12) 0.83023(10) 0.46141(15) 0.0356(3) Uani 1 1 d . . . . .
C7 C 0.35133(11) 0.64257(11) 0.48895(15) 0.0364(3) Uani 1 1 d . . . . .
C6 C 0.29668(12) 0.83426(10) 0.52299(15) 0.0356(3) Uani 1 1 d . . . . .
H5 H 0.4811(16) 0.8920(15) 0.433(2) 0.056(4) Uiso 1 1 d . . . . .
H6 H 0.2468(16) 0.9002(15) 0.553(2) 0.052(4) Uiso 1 1 d . . . . .
H1 H 0.5348(18) 0.6826(16) 0.402(2) 0.058(4) Uiso 1 1 d . . . . .
H2 H 0.1743(18) 0.6923(16) 0.582(2) 0.059(5) Uiso 1 1 d . . . . .
H7 H 0.3455(16) 0.5560(17) 0.489(2) 0.064(5) Uiso 1 1 d . . . . .
H4 H 0.9921(16) 0.5146(16) 0.256(2) 0.076(6) 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 C1 1.2592(11) . ?
O3 C3 1.2346(11) . ?
O4 C4 1.3061(11) . ?
O2 C2 1.2140(11) . ?
C3 C4 1.4446(12) . ?
C3 C2 1.5045(13) . ?
C2 C1 1.4926(12) . ?
C4 C1 1.4179(12) . ?
N1 C7 1.3243(13) . ?
N1 C5 1.3698(14) . ?
N2 C7 1.3215(14) . ?
N2 C6 1.3695(14) . ?
C5 C6 1.3549(16) . ?

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
O3 C3 C4 136.95(8) . . ?
O3 C3 C2 134.47(8) . . ?
C4 C3 C2 88.59(7) . . ?
O2 C2 C1 136.77(8) . . ?
O2 C2 C3 135.21(8) . . ?
C1 C2 C3 88.01(7) . . ?
O4 C4 C1 129.65(8) . . ?
O4 C4 C3 137.01(8) . . ?
C1 C4 C3 93.34(7) . . ?
O1 C1 C4 134.31(8) . . ?
O1 C1 C2 135.62(8) . . ?
C4 C1 C2 90.06(7) . . ?
C7 N1 C5 108.68(9) . . ?
C7 N2 C6 109.01(9) . . ?
C6 C5 N1 107.03(9) . . ?
N2 C7 N1 108.62(10) . . ?
C5 C6 N2 106.67(9) . . ?

_refine_diff_density_max         0.368
_refine_diff_density_min         -0.158
_refine_diff_density_rms         0.036



####################################################################### 
# 
# 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_SQIM250K_HT
_database_code_depnum_ccdc_archive 'CCDC 2383785'
loop_
_audit_author_name
_audit_author_address
'Dinabandhu Das'
;Jawaharlal Nehru University, New Delhi
India
;
_audit_update_record             
;
2024-09-13 deposited with the CCDC.	2024-11-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C4 H O4, C3 H5 N2'
_chemical_formula_sum            'C7 H6 N2 O4'
_chemical_formula_weight         182.14

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   9.3773(10)
_cell_length_b                   10.9848(13)
_cell_length_c                   7.5143(8)
_cell_angle_alpha                90
_cell_angle_beta                 100.458(4)
_cell_angle_gamma                90
_cell_volume                     761.17(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    250(2)
_cell_measurement_reflns_used    7751
_cell_measurement_theta_min      2.21
_cell_measurement_theta_max      28.36

_exptl_crystal_description       Block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.589
_exptl_crystal_F_000             376
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.298
_exptl_crystal_size_mid          0.258
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.133
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.7138
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      250(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   Microfocus
_diffrn_measurement_device_type  'Bruker APEX-III CMOS detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13588
_diffrn_reflns_av_unetI/netI     0.0124
_diffrn_reflns_av_R_equivalents  0.0201
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.884
_diffrn_reflns_theta_max         28.381
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 0.981
_reflns_number_total             1879
_reflns_number_gt                1737
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    'XSeed (Barbour 2017)'
_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)+(0.0627P)²+0.1165P] 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_number_reflns         1879
_refine_ls_number_parameters     142
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0384
_refine_ls_R_factor_gt           0.0357
_refine_ls_wR_factor_ref         0.1080
_refine_ls_wR_factor_gt          0.1052
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_restrained_S_all      1.094
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 1.02327(7) 0.87787(6) 0.17875(11) 0.0334(2) Uani 1 1 d . . . . .
O3 O 0.69528(8) 0.60845(7) 0.33440(12) 0.0376(2) Uani 1 1 d . . . . .
O4 O 1.01532(8) 0.59356(7) 0.21361(12) 0.0377(2) Uani 1 1 d . . . . .
O2 O 0.70536(8) 0.90143(7) 0.29596(13) 0.0414(2) Uani 1 1 d . . . . .
C3 C 0.78249(10) 0.68211(8) 0.29175(13) 0.0261(2) Uani 1 1 d . . . . .
C2 C 0.78626(10) 0.81859(8) 0.27485(13) 0.0273(2) Uani 1 1 d . . . . .
C4 C 0.92262(10) 0.67744(8) 0.23876(13) 0.0257(2) Uani 1 1 d . . . . .
C1 C 0.93074(10) 0.80578(8) 0.22140(13) 0.0253(2) Uani 1 1 d . . . . .
N1 N 0.45525(10) 0.70975(9) 0.44164(13) 0.0334(2) Uani 1 1 d . . . . .
N2 N 0.25435(10) 0.71588(9) 0.53920(13) 0.0337(2) Uani 1 1 d . . . . .
C5 C 0.42330(12) 0.83009(10) 0.46155(15) 0.0359(3) Uani 1 1 d . . . . .
C7 C 0.35130(11) 0.64261(11) 0.48903(15) 0.0368(3) Uani 1 1 d . . . . .
C6 C 0.29674(12) 0.83413(11) 0.52311(15) 0.0362(3) Uani 1 1 d . . . . .
H4 H 0.9917(15) 0.5143(16) 0.255(2) 0.074(6) Uiso 1 1 d . . . . .
H2 H 0.1733(18) 0.6921(16) 0.581(2) 0.061(5) Uiso 1 1 d . . . . .
H1 H 0.5346(18) 0.6815(16) 0.402(2) 0.059(4) Uiso 1 1 d . . . . .
H7 H 0.3464(16) 0.5559(18) 0.489(2) 0.066(5) Uiso 1 1 d . . . . .
H5 H 0.4809(16) 0.8920(15) 0.433(2) 0.056(4) Uiso 1 1 d . . . . .
H6 H 0.2470(16) 0.8995(15) 0.553(2) 0.054(4) 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 C1 1.2585(11) . ?
O3 C3 1.2334(11) . ?
O4 C4 1.3039(11) . ?
O2 C2 1.2135(11) . ?
C3 C4 1.4415(12) . ?
C3 C2 1.5055(13) . ?
C2 C1 1.4880(12) . ?
C4 C1 1.4191(12) . ?
N1 C7 1.3217(13) . ?
N1 C5 1.3696(14) . ?
N2 C7 1.3194(14) . ?
N2 C6 1.3702(15) . ?
C5 C6 1.3505(16) . ?

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
O3 C3 C4 136.81(9) . . ?
O3 C3 C2 134.59(8) . . ?
C4 C3 C2 88.60(7) . . ?
O2 C2 C1 136.68(9) . . ?
O2 C2 C3 135.32(8) . . ?
C1 C2 C3 88.00(7) . . ?
O4 C4 C1 129.82(8) . . ?
O4 C4 C3 136.92(8) . . ?
C1 C4 C3 93.26(7) . . ?
O1 C1 C4 134.39(8) . . ?
O1 C1 C2 135.47(8) . . ?
C4 C1 C2 90.14(7) . . ?
C7 N1 C5 108.82(9) . . ?
C7 N2 C6 109.10(9) . . ?
C6 C5 N1 107.00(9) . . ?
N2 C7 N1 108.46(10) . . ?
C5 C6 N2 106.62(9) . . ?

_refine_diff_density_max         0.378
_refine_diff_density_min         -0.169
_refine_diff_density_rms         0.036



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Mixture of Methanol and Water'
####################################################################### 
# 
# 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_SQIM300K_HT
_database_code_depnum_ccdc_archive 'CCDC 2383786'
loop_
_audit_author_name
_audit_author_address
'Dinabandhu Das'
;Jawaharlal Nehru University, New Delhi
India
;
_audit_update_record             
;
2024-09-13 deposited with the CCDC.	2024-11-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C4 H O4, C3 H5 N2'
_chemical_formula_sum            'C7 H6 N2 O4'
_chemical_formula_weight         182.14

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   9.3808(10)
_cell_length_b                   10.9778(13)
_cell_length_c                   7.5597(8)
_cell_angle_alpha                90
_cell_angle_beta                 100.221(4)
_cell_angle_gamma                90
_cell_volume                     766.15(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    300(2)
_cell_measurement_reflns_used    7159
_cell_measurement_theta_min      2.21
_cell_measurement_theta_max      28.38

_exptl_crystal_description       Block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.579
_exptl_crystal_F_000             376
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.298
_exptl_crystal_size_mid          0.258
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.132
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.7122
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      300(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   Microfocus
_diffrn_measurement_device_type  'Bruker APEX-III CMOS detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13708
_diffrn_reflns_av_unetI/netI     0.0130
_diffrn_reflns_av_R_equivalents  0.0213
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.883
_diffrn_reflns_theta_max         28.387
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measured_fraction_theta_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_point_group_measured_fraction_full 0.982
_reflns_number_total             1889
_reflns_number_gt                1702
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    'XSeed (Barbour 2017)'
_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)+(0.0623P)²+0.1410P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1889
_refine_ls_number_parameters     142
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0417
_refine_ls_R_factor_gt           0.0375
_refine_ls_wR_factor_ref         0.1112
_refine_ls_wR_factor_gt          0.1069
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_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
O1 O 1.02313(8) 0.87781(7) 0.17968(12) 0.0407(2) Uani 1 1 d . . . . .
O3 O 0.69547(9) 0.60840(7) 0.33453(13) 0.0463(2) Uani 1 1 d . . . . .
O4 O 1.01549(9) 0.59387(7) 0.21443(14) 0.0463(3) Uani 1 1 d . . . . .
O2 O 0.70528(9) 0.90104(7) 0.29636(15) 0.0510(3) Uani 1 1 d . . . . .
C3 C 0.78259(10) 0.68201(9) 0.29208(14) 0.0318(2) Uani 1 1 d . . . . .
C2 C 0.78625(11) 0.81846(9) 0.27536(14) 0.0332(2) Uani 1 1 d . . . . .
C4 C 0.92266(10) 0.67753(9) 0.23944(14) 0.0313(2) Uani 1 1 d . . . . .
C1 C 0.93070(10) 0.80576(9) 0.22220(14) 0.0306(2) Uani 1 1 d . . . . .
N1 N 0.45497(11) 0.70956(10) 0.44228(14) 0.0414(3) Uani 1 1 d . . . . .
N2 N 0.25467(11) 0.71553(10) 0.53992(14) 0.0418(3) Uani 1 1 d . . . . .
C5 C 0.42314(13) 0.82952(11) 0.46217(17) 0.0445(3) Uani 1 1 d . . . . .
C7 C 0.35115(12) 0.64257(12) 0.48953(17) 0.0455(3) Uani 1 1 d . . . . .
C6 C 0.29688(13) 0.83357(12) 0.52359(17) 0.0445(3) Uani 1 1 d . . . . .
H4 H 0.9921(16) 0.5140(16) 0.255(2) 0.082(6) Uiso 1 1 d . . . . .
H2 H 0.1732(19) 0.6924(18) 0.583(2) 0.073(5) Uiso 1 1 d . . . . .
H7 H 0.3460(17) 0.5552(19) 0.489(2) 0.079(6) Uiso 1 1 d . . . . .
H1 H 0.5343(19) 0.6818(17) 0.404(2) 0.069(5) Uiso 1 1 d . . . . .
H5 H 0.4812(18) 0.8909(16) 0.435(2) 0.065(5) Uiso 1 1 d . . . . .
H6 H 0.2477(17) 0.8979(16) 0.554(2) 0.066(5) 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 C1 1.2568(11) . ?
O3 C3 1.2316(12) . ?
O4 C4 1.3023(12) . ?
O2 C2 1.2111(12) . ?
C3 C4 1.4397(13) . ?
C3 C2 1.5042(14) . ?
C2 C1 1.4868(13) . ?
C4 C1 1.4169(13) . ?
N1 C7 1.3192(15) . ?
N1 C5 1.3646(16) . ?
N2 C7 1.3145(15) . ?
N2 C6 1.3669(17) . ?
C5 C6 1.3475(17) . ?

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
O3 C3 C4 136.88(9) . . ?
O3 C3 C2 134.53(9) . . ?
C4 C3 C2 88.58(7) . . ?
O2 C2 C1 136.76(9) . . ?
O2 C2 C3 135.25(9) . . ?
C1 C2 C3 87.99(7) . . ?
O4 C4 C1 129.74(9) . . ?
O4 C4 C3 136.95(9) . . ?
C1 C4 C3 93.31(8) . . ?
O1 C1 C4 134.36(9) . . ?
O1 C1 C2 135.51(9) . . ?
C4 C1 C2 90.13(8) . . ?
C7 N1 C5 108.77(10) . . ?
C7 N2 C6 109.03(10) . . ?
C6 C5 N1 107.01(10) . . ?
N2 C7 N1 108.55(12) . . ?
C5 C6 N2 106.64(10) . . ?

_refine_diff_density_max         0.341
_refine_diff_density_min         -0.150
_refine_diff_density_rms         0.034



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Mixture of Methanol and Water'
####################################################################### 
# 
# 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_SQIM300K_LT
_database_code_depnum_ccdc_archive 'CCDC 2383781'
loop_
_audit_author_name
_audit_author_address
'Dinabandhu Das'
;Jawaharlal Nehru University, New Delhi
India
;
_audit_update_record             
;
2024-09-13 deposited with the CCDC.	2024-11-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C4 H O4, C3 H5 N2'
_chemical_formula_sum            'C7 H6 N2 O4'
_chemical_formula_weight         182.14

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   9.4094(10)
_cell_length_b                   10.9728(12)
_cell_length_c                   7.5549(10)
_cell_angle_alpha                90
_cell_angle_beta                 100.201(4)
_cell_angle_gamma                90
_cell_volume                     767.69(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    300(2)
_cell_measurement_reflns_used    7373
_cell_measurement_theta_min      2.88
_cell_measurement_theta_max      28.36

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.576
_exptl_crystal_F_000             376
_exptl_transmission_factor_min   ?
_exptl_crystal_size_max          0.258
_exptl_crystal_size_mid          0.257
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.132
_shelx_estimated_absorpt_T_min   0.7125
_shelx_estimated_absorpt_T_max   0.7457
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      300(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   Microfocus
_diffrn_measurement_device_type  'Bruker APEX-III CMOS detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13186
_diffrn_reflns_av_unetI/netI     0.0129
_diffrn_reflns_av_R_equivalents  0.0208
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.878
_diffrn_reflns_theta_max         28.362
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measured_fraction_theta_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_point_group_measured_fraction_full 0.977
_reflns_number_total             1883
_reflns_number_gt                1719
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_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)+(0.0646P)²+0.1304P] 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_number_reflns         1883
_refine_ls_number_parameters     142
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0405
_refine_ls_R_factor_gt           0.0376
_refine_ls_wR_factor_ref         0.1096
_refine_ls_wR_factor_gt          0.1068
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_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
O1 O 1.02322(8) 0.87778(6) 0.17975(12) 0.0403(2) Uani 1 1 d . . . . .
O3 O 0.69548(8) 0.60832(7) 0.33445(13) 0.0459(2) Uani 1 1 d . . . . .
O4 O 1.01558(8) 0.59372(7) 0.21452(13) 0.0456(2) Uani 1 1 d . . . . .
O2 O 0.70539(9) 0.90112(7) 0.29642(14) 0.0505(3) Uani 1 1 d . . . . .
C3 C 0.78270(10) 0.68192(8) 0.29227(13) 0.0314(2) Uani 1 1 d . . . . .
C2 C 0.78633(10) 0.81841(8) 0.27542(14) 0.0326(2) Uani 1 1 d . . . . .
C4 C 0.92271(10) 0.67752(8) 0.23961(13) 0.0307(2) Uani 1 1 d . . . . .
C1 C 0.93076(10) 0.80572(8) 0.22218(13) 0.0299(2) Uani 1 1 d . . . . .
N1 N 0.45512(10) 0.70951(9) 0.44227(14) 0.0409(2) Uani 1 1 d . . . . .
N2 N 0.25472(10) 0.71559(10) 0.53984(14) 0.0412(3) Uani 1 1 d . . . . .
C5 C 0.42322(13) 0.82962(11) 0.46203(17) 0.0440(3) Uani 1 1 d . . . . .
C7 C 0.35121(12) 0.64245(12) 0.48964(17) 0.0448(3) Uani 1 1 d . . . . .
C6 C 0.29691(13) 0.83366(11) 0.52363(16) 0.0440(3) Uani 1 1 d . . . . .
H4 H 0.9920(16) 0.5142(16) 0.256(2) 0.087(6) Uiso 1 1 d . . . . .
H5 H 0.4815(17) 0.8915(15) 0.434(2) 0.067(5) Uiso 1 1 d . . . . .
H6 H 0.2471(17) 0.8988(16) 0.553(2) 0.068(5) Uiso 1 1 d . . . . .
H2 H 0.1728(19) 0.6927(17) 0.581(2) 0.071(5) Uiso 1 1 d . . . . .
H1 H 0.5352(18) 0.6816(17) 0.403(2) 0.071(5) Uiso 1 1 d . . . . .
H7 H 0.3459(17) 0.5543(19) 0.488(2) 0.083(6) 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 C1 1.2585(11) . ?
O3 C3 1.2329(11) . ?
O4 C4 1.3053(11) . ?
O2 C2 1.2131(12) . ?
C3 C4 1.4429(12) . ?
C3 C2 1.5040(13) . ?
C2 C1 1.4905(13) . ?
C4 C1 1.4161(12) . ?
N1 C7 1.3227(14) . ?
N1 C5 1.3657(15) . ?
N2 C7 1.3168(15) . ?
N2 C6 1.3669(16) . ?
C5 C6 1.3517(17) . ?

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
O3 C3 C4 137.01(9) . . ?
O3 C3 C2 134.46(9) . . ?
C4 C3 C2 88.54(7) . . ?
O2 C2 C1 136.78(9) . . ?
O2 C2 C3 135.21(9) . . ?
C1 C2 C3 88.01(7) . . ?
O4 C4 C1 129.65(8) . . ?
O4 C4 C3 136.98(8) . . ?
C1 C4 C3 93.37(7) . . ?
O1 C1 C4 134.31(9) . . ?
O1 C1 C2 135.61(8) . . ?
C4 C1 C2 90.08(7) . . ?
C7 N1 C5 108.66(9) . . ?
C7 N2 C6 109.02(10) . . ?
C6 C5 N1 107.03(9) . . ?
N2 C7 N1 108.62(11) . . ?
C5 C6 N2 106.67(10) . . ?

_refine_diff_density_max         0.314
_refine_diff_density_min         -0.155
_refine_diff_density_rms         0.034



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Mixture of Methanol and Water'
####################################################################### 
# 
# 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_SQIM350K_HT
_database_code_depnum_ccdc_archive 'CCDC 2383787'
loop_
_audit_author_name
_audit_author_address
'Dinabandhu Das'
;Jawaharlal Nehru University, New Delhi
India
;
_audit_update_record             
;
2024-09-13 deposited with the CCDC.	2024-11-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C4 H O4, C3 H5 N2'
_chemical_formula_sum            'C7 H6 N2 O4'
_chemical_formula_weight         182.14

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   9.3883(10)
_cell_length_b                   10.9737(14)
_cell_length_c                   7.6099(9)
_cell_angle_alpha                90
_cell_angle_beta                 99.955(4)
_cell_angle_gamma                90
_cell_volume                     772.20(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    350(2)
_cell_measurement_reflns_used    6519
_cell_measurement_theta_min      2.20
_cell_measurement_theta_max      28.37

_exptl_crystal_description       Block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.567
_exptl_crystal_F_000             376
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.298
_exptl_crystal_size_mid          0.258
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.131
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.7075
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      350(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   Microfocus
_diffrn_measurement_device_type  'Bruker APEX-III CMOS detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13900
_diffrn_reflns_av_unetI/netI     0.0135
_diffrn_reflns_av_R_equivalents  0.0224
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.881
_diffrn_reflns_theta_max         28.369
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.984
_reflns_number_total             1911
_reflns_number_gt                1651
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    'XSeed (Barbour 2017)'
_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)+(0.0654P)²+0.1307P] 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_number_reflns         1911
_refine_ls_number_parameters     142
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0461
_refine_ls_R_factor_gt           0.0405
_refine_ls_wR_factor_ref         0.1215
_refine_ls_wR_factor_gt          0.1156
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 1.02286(9) 0.87797(7) 0.18111(14) 0.0498(3) Uani 1 1 d . . . . .
O3 O 0.69577(10) 0.60811(8) 0.33449(15) 0.0564(3) Uani 1 1 d . . . . .
O4 O 1.01576(10) 0.59428(8) 0.21531(15) 0.0562(3) Uani 1 1 d . . . . .
O2 O 0.70511(10) 0.90061(8) 0.29711(17) 0.0626(3) Uani 1 1 d . . . . .
C3 C 0.78286(11) 0.68187(10) 0.29274(16) 0.0387(3) Uani 1 1 d . . . . .
C2 C 0.78617(12) 0.81811(10) 0.27627(16) 0.0406(3) Uani 1 1 d . . . . .
C4 C 0.92275(11) 0.67776(10) 0.24021(16) 0.0380(3) Uani 1 1 d . . . . .
C1 C 0.93061(11) 0.80565(9) 0.22332(15) 0.0373(3) Uani 1 1 d . . . . .
N1 N 0.45455(12) 0.70944(11) 0.44285(16) 0.0511(3) Uani 1 1 d . . . . .
N2 N 0.25502(12) 0.71539(12) 0.54046(16) 0.0517(3) Uani 1 1 d . . . . .
C5 C 0.42290(15) 0.82881(13) 0.4627(2) 0.0553(4) Uani 1 1 d . . . . .
C7 C 0.35083(14) 0.64253(14) 0.4900(2) 0.0559(4) Uani 1 1 d . . . . .
C6 C 0.29715(16) 0.83279(14) 0.5242(2) 0.0552(4) Uani 1 1 d . . . . .
H4 H 0.9925(16) 0.5144(17) 0.256(2) 0.085(6) Uiso 1 1 d . . . . .
H2 H 0.173(2) 0.692(2) 0.583(3) 0.089(6) Uiso 1 1 d . . . . .
H1 H 0.534(2) 0.6818(19) 0.404(3) 0.082(6) Uiso 1 1 d . . . . .
H5 H 0.481(2) 0.8899(18) 0.437(2) 0.081(6) Uiso 1 1 d . . . . .
H6 H 0.2479(19) 0.8967(19) 0.553(2) 0.081(6) Uiso 1 1 d . . . . .
H7 H 0.346(2) 0.555(2) 0.491(3) 0.101(7) 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 C1 1.2566(12) . ?
O3 C3 1.2306(13) . ?
O4 C4 1.3018(13) . ?
O2 C2 1.2107(13) . ?
C3 C4 1.4381(14) . ?
C3 C2 1.5011(15) . ?
C2 C1 1.4863(14) . ?
C4 C1 1.4124(15) . ?
N1 C7 1.3178(16) . ?
N1 C5 1.3574(19) . ?
N2 C7 1.3097(18) . ?
N2 C6 1.3596(19) . ?
C5 C6 1.344(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
O3 C3 C4 136.93(10) . . ?
O3 C3 C2 134.50(10) . . ?
C4 C3 C2 88.56(8) . . ?
O2 C2 C1 136.72(10) . . ?
O2 C2 C3 135.34(10) . . ?
C1 C2 C3 87.94(8) . . ?
O4 C4 C1 129.72(9) . . ?
O4 C4 C3 136.91(10) . . ?
C1 C4 C3 93.37(8) . . ?
O1 C1 C4 134.42(10) . . ?
O1 C1 C2 135.45(10) . . ?
C4 C1 C2 90.13(8) . . ?
C7 N1 C5 108.74(11) . . ?
C7 N2 C6 109.05(12) . . ?
C6 C5 N1 107.00(12) . . ?
N2 C7 N1 108.48(13) . . ?
C5 C6 N2 106.72(12) . . ?

_refine_diff_density_max         0.298
_refine_diff_density_min         -0.147
_refine_diff_density_rms         0.032



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Mixture of Methanol and Water'
####################################################################### 
# 
# 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_SQIM150K_LT
_database_code_depnum_ccdc_archive 'CCDC 2383893'
loop_
_audit_author_name
_audit_author_address
'Dinabandhu Das'
;Jawaharlal Nehru University, New Delhi
India
;
_audit_update_record             
;
2024-09-13 deposited with the CCDC.	2024-11-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/2
_shelx_SHELXL_version_number     2019/2
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C4 H O4, C3 H5 N2'
_chemical_formula_sum            'C7 H6 N2 O4'
_chemical_formula_weight         182.14

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   7.264(4)
_cell_length_b                   21.365(11)
_cell_length_c                   9.973(5)
_cell_angle_alpha                90
_cell_angle_beta                 100.19(2)
_cell_angle_gamma                90
_cell_volume                     1523.4(15)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    1123
_cell_measurement_theta_min      3.43
_cell_measurement_theta_max      25.85

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.588
_exptl_crystal_F_000             752
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.228
_exptl_crystal_size_mid          0.198
_exptl_crystal_size_min          0.108
_exptl_absorpt_coefficient_mu    0.133
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.5116
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   Microfocus
_diffrn_measurement_device_type  'Bruker APEX-III CMOS detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5722
_diffrn_reflns_av_unetI/netI     0.1318
_diffrn_reflns_av_R_equivalents  0.0887
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         1.906
_diffrn_reflns_theta_max         26.536
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.855
_diffrn_measured_fraction_theta_full 0.881
_diffrn_reflns_Laue_measured_fraction_max 0.855
_diffrn_reflns_Laue_measured_fraction_full 0.881
_diffrn_reflns_point_group_measured_fraction_max 0.855
_diffrn_reflns_point_group_measured_fraction_full 0.881
_reflns_number_total             2709
_reflns_number_gt                1175
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    'XSEED (Barbour 2017)'
_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   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2709
_refine_ls_number_parameters     243
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.2746
_refine_ls_R_factor_gt           0.1629
_refine_ls_wR_factor_ref         0.4805
_refine_ls_wR_factor_gt          0.4178
_refine_ls_goodness_of_fit_ref   1.385
_refine_ls_restrained_S_all      1.385
_refine_ls_shift/su_max          2.614
_refine_ls_shift/su_mean         0.018

_vrf_SHFSU01_SQIM150K_LT         
;
PROBLEM: The absolute value of parameter shift to su ratio > 0.20
RESPONSE: The single crystal used for data collection at 150 K was obtained from the pristine 
crystals after jumping followed by shearing below 190K. Hence, there may be twining in the crystal
for which refinement is not completed.
;
_vrf_PLAT029_SQIM150K_LT         
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.881 Why?  
RESPONSE: The single crystal used for data collection at 150 K was obtained from the pristine 
crystals after jumping followed by shearing below 190K. Hence, there may be twining in the crystal
for which refinement is not completed.

;
_vrf_PLAT080_SQIM150K_LT         
;
PROBLEM: Maximum Shift/Error ............................       2.61 Why ? 
RESPONSE: The single crystal used for data collection at 150 K was obtained from the pristine 
crystals after jumping followed by shearing below 190K. Hence, there may be twining in the crystal
for which refinement is not completed.

;
_vrf_PLAT084_SQIM150K_LT         
;
PROBLEM: High wR2 Value (i.e. > 0.25) ...................       0.48 Report
RESPONSE: The single crystal used for data collection at 150 K was obtained from the pristine 
crystals after jumping followed by shearing below 190K. Hence, there may be twining in the crystal
for which refinement is not completed.
;
_vrf_PLAT203_SQIM150K_LT         
;
PROBLEM: Negative Isotropic ADP for H1        ...........     -0.001 Report
RESPONSE: The single crystal used for data collection at 150 K was obtained from the pristine 
crystals after jumping followed by shearing below 190K. Hence, there may be twining in the crystal
for which refinement is not completed.

;
_vrf_PLAT213_SQIM150K_LT         
;
PROBLEM: Atom O8              has ADP max/min Ratio .....        6.3 prolat
RESPONSE: The single crystal used for data collection at 150 K was obtained from the pristine 
crystals after jumping followed by shearing below 190K. Hence, there may be twining in the crystal
for which refinement is not completed.

;
_vrf_PLAT214_SQIM150K_LT         
;
PROBLEM: Atom C14       (Anion/Solvent) ADP max/min Ratio        9.3 oblate
RESPONSE: The single crystal used for data collection at 150 K was obtained from the pristine 
crystals after jumping followed by shearing below 190K. Hence, there may be twining in the crystal
for which refinement is not completed.

;
_vrf_PLAT415_SQIM150K_LT         
;
PROBLEM: Short Inter D-H..H-X       H2       ..H13      .       1.83 Ang.  
RESPONSE: The single crystal used for data collection at 150 K was obtained from the pristine 
crystals after jumping followed by shearing below 190K. Hence, there may be twining in the crystal
for which refinement is not completed.

;
_vrf_PLAT082_SQIM150K_LT         
;
PROBLEM: High R1 Value ..................................       0.16 Report
RESPONSE:The single crystal used for data collection at 150 K was obtained from the pristine 
crystals after jumping followed by shearing below 190K. Hence, there may be twining in the crystal
for which refinement is not completed.

;
_vrf_PLAT097_SQIM150K_LT         
;
PROBLEM: Large Reported Max.  (Positive) Residual Density       1.47 eA-3  
RESPONSE: The single crystal used for data collection at 150 K was obtained from the pristine 
crystals after jumping followed by shearing below 190K. Hence, there may be twining in the crystal
for which refinement is not completed.

;
_vrf_PLAT212_SQIM150K_LT         
;
PROBLEM: ADP of Atom C9        is N.P.D. or (nearly) 2D .     Please Check 
RESPONSE:The single crystal used for data collection at 150 K was obtained from the pristine 
crystals after jumping followed by shearing below 190K. Hence, there may be twining in the crystal
for which refinement is not completed.

;
_vrf_PLAT250_SQIM150K_LT         
;
PROBLEM: Large U3/U1 Ratio for <U(i,j)> Tensor(Resd    1)        4.3 Note  
RESPONSE: The single crystal used for data collection at 150 K was obtained from the pristine 
crystals after jumping followed by shearing below 190K. Hence, there may be twining in the crystal
for which refinement is not completed.

;
_vrf_PLAT340_SQIM150K_LT         
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............     0.0118 Ang.  
RESPONSE: The single crystal used for data collection at 150 K was obtained from the pristine 
crystals after jumping followed by shearing below 190K. Hence, there may be twining in the crystal
for which refinement is not completed.

;
_vrf_PLAT420_SQIM150K_LT         
;
PROBLEM: D-H Bond Without Acceptor  O8       --H1 .     Please Check 
RESPONSE: The single crystal used for data collection at 150 K was obtained from the pristine 
crystals after jumping followed by shearing below 190K. Hence, there may be twining in the crystal
for which refinement is not completed.

;
_vrf_PLAT911_SQIM150K_LT         
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600        331 Report
RESPONSE: The single crystal used for data collection at 150 K was obtained from the pristine 
crystals after jumping followed by shearing below 190K. Hence, there may be twining in the crystal
for which refinement is not completed.

;
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
O6 O 0.3655(10) 0.7119(2) 0.5980(6) 0.036(2) Uani 1 1 d . . . . .
O5 O 0.6363(9) 0.7204(3) 0.8887(6) 0.033(2) Uani 1 1 d . . . . .
O7 O 0.3744(9) 0.5581(2) 0.6202(6) 0.033(2) Uani 1 1 d . . . . .
O2 O -0.1138(9) 0.6050(2) 0.1198(7) 0.036(2) Uani 1 1 d . . . . .
O1 O 0.1519(9) 0.5960(3) 0.4037(6) 0.037(2) Uani 1 1 d D . . . .
O8 O 0.6652(9) 0.5677(3) 0.9014(6) 0.040(2) Uani 1 1 d . . . . .
O4 O 0.1322(10) 0.4423(3) 0.3893(7) 0.047(2) Uani 1 1 d . . . . .
N4 N 0.0213(11) 0.2237(3) 0.2915(8) 0.032(2) Uani 1 1 d . . . . .
H4A H 0.039321 0.184184 0.315351 0.039 Uiso 1 1 calc R U . . .
N2 N 0.4617(11) 0.3388(3) 0.7093(7) 0.034(2) Uani 1 1 d . . . . .
H2A H 0.438173 0.300096 0.681132 0.040 Uiso 1 1 calc R U . . .
N3 N 0.0326(11) 0.3234(3) 0.2931(8) 0.040(3) Uani 1 1 d . . . . .
H3A H 0.061152 0.361944 0.320349 0.047 Uiso 1 1 calc R U . . .
N1 N 0.4657(11) 0.4385(3) 0.7168(8) 0.045(3) Uani 1 1 d . . . . .
H1A H 0.442983 0.478009 0.694502 0.054 Uiso 1 1 calc R U . . .
O3 O -0.1490(11) 0.4530(3) 0.1005(7) 0.066(3) Uani 1 1 d . . . . .
C11 C 0.4023(13) 0.3906(4) 0.6381(10) 0.030(3) Uani 1 1 d . . . . .
H11 H 0.329468 0.392344 0.549142 0.036 Uiso 1 1 calc R U . . .
C9 C 0.5679(12) 0.4197(3) 0.8335(9) 0.023(2) Uani 1 1 d . . . . .
H9 H 0.630555 0.446210 0.903383 0.027 Uiso 1 1 calc R U . . .
C2 C -0.0503(13) 0.5601(4) 0.1902(9) 0.027(3) Uani 1 1 d . . . . .
C5 C 0.5683(12) 0.6769(3) 0.8178(9) 0.022(2) Uani 1 1 d . . . . .
C1 C 0.0703(12) 0.5509(3) 0.3195(9) 0.024(3) Uani 1 1 d . . . . .
C8 C 0.5719(12) 0.6081(3) 0.8180(9) 0.021(2) Uani 1 1 d . . . . .
C4 C 0.0628(12) 0.4855(3) 0.3151(9) 0.022(2) Uani 1 1 d . . . . .
C6 C 0.4400(13) 0.6721(3) 0.6826(9) 0.027(3) Uani 1 1 d . . . . .
C7 C 0.4496(13) 0.6040(4) 0.6935(10) 0.031(3) Uani 1 1 d . . . . .
C10 C 0.5679(14) 0.3562(4) 0.8364(11) 0.038(3) Uani 1 1 d . . . . .
H10 H 0.625998 0.329548 0.907762 0.046 Uiso 1 1 calc R U . . .
C14 C -0.0737(14) 0.3073(4) 0.1749(10) 0.040(3) Uani 1 1 d . . . . .
H14 H -0.131144 0.335499 0.106425 0.048 Uiso 1 1 calc R U . . .
C3 C -0.0658(13) 0.4900(4) 0.1803(9) 0.029(3) Uani 1 1 d . . . . .
C12 C 0.0876(15) 0.2726(4) 0.3616(11) 0.041(3) Uani 1 1 d . . . . .
H12 H 0.164269 0.271501 0.449224 0.049 Uiso 1 1 calc R U . . .
C13 C -0.0857(14) 0.2469(5) 0.1693(11) 0.040(3) Uani 1 1 d . . . . .
H13 H -0.153333 0.222775 0.096969 0.048 Uiso 1 1 calc R U . . .
H1 H 0.605(9) 0.530(3) 0.884(7) -0.001(17) Uiso 1 1 d . . . . .
H2 H 0.16(3) 0.638(2) 0.378(15) 0.35(15) Uiso 1 1 d 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
O6 C6 1.251(9) . ?
O5 C5 1.219(9) . ?
O7 C7 1.287(9) . ?
O2 C2 1.228(9) . ?
O1 C1 1.344(9) . ?
O8 C8 1.302(8) . ?
O4 C4 1.233(8) . ?
N4 C12 1.301(10) . ?
N4 C13 1.414(12) . ?
N2 C11 1.344(9) . ?
N2 C10 1.412(12) . ?
N3 C12 1.308(11) . ?
N3 C14 1.335(10) . ?
N1 C11 1.323(10) . ?
N1 C9 1.328(10) . ?
O3 C3 1.206(9) . ?
C9 C10 1.356(10) . ?
C2 C1 1.439(11) . ?
C2 C3 1.505(11) . ?
C5 C8 1.469(10) . ?
C5 C6 1.501(12) . ?
C1 C4 1.400(9) . ?
C1 C3 2.028(12) . ?
C8 C7 1.396(12) . ?
C8 C6 2.038(11) . ?
C4 C3 1.498(12) . ?
C6 C7 1.459(10) . ?
C14 C13 1.294(13) . ?

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
C12 N4 C13 106.0(8) . . ?
C11 N2 C10 109.3(7) . . ?
C12 N3 C14 108.8(8) . . ?
C11 N1 C9 111.5(7) . . ?
N1 C11 N2 106.2(8) . . ?
N1 C9 C10 108.7(8) . . ?
O2 C2 C1 136.6(7) . . ?
O2 C2 C3 136.3(7) . . ?
C1 C2 C3 87.1(6) . . ?
O5 C5 C8 139.2(8) . . ?
O5 C5 C6 134.1(7) . . ?
C8 C5 C6 86.6(6) . . ?
O1 C1 C4 138.2(7) . . ?
O1 C1 C2 126.4(6) . . ?
C4 C1 C2 95.4(7) . . ?
O1 C1 C3 174.2(6) . . ?
C4 C1 C3 47.6(5) . . ?
C2 C1 C3 47.8(4) . . ?
O8 C8 C7 134.7(7) . . ?
O8 C8 C5 132.1(8) . . ?
C7 C8 C5 93.1(6) . . ?
O8 C8 C6 176.6(9) . . ?
C7 C8 C6 45.7(4) . . ?
C5 C8 C6 47.3(4) . . ?
O4 C4 C1 135.9(8) . . ?
O4 C4 C3 135.3(7) . . ?
C1 C4 C3 88.8(6) . . ?
O6 C6 C7 137.4(8) . . ?
O6 C6 C5 133.3(7) . . ?
C7 C6 C5 89.2(6) . . ?
O6 C6 C8 177.6(9) . . ?
C7 C6 C8 43.2(5) . . ?
C5 C6 C8 46.0(4) . . ?
O7 C7 C8 133.8(7) . . ?
O7 C7 C6 135.1(8) . . ?
C8 C7 C6 91.1(7) . . ?
C9 C10 N2 104.3(7) . . ?
C13 C14 N3 108.6(9) . . ?
O3 C3 C4 135.2(8) . . ?
O3 C3 C2 136.0(8) . . ?
C4 C3 C2 88.7(6) . . ?
O3 C3 C1 178.1(10) . . ?
C4 C3 C1 43.6(4) . . ?
C2 C3 C1 45.1(4) . . ?
N4 C12 N3 109.7(9) . . ?
C14 C13 N4 106.9(9) . . ?

_refine_diff_density_max         1.470
_refine_diff_density_min         -0.703
_refine_diff_density_rms         0.184



####################################################################### 
# 
# 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_SQIM400K_HT
_database_code_depnum_ccdc_archive 'CCDC 2383788'
loop_
_audit_author_name
_audit_author_address
'Dinabandhu Das'
;Jawaharlal Nehru University, New Delhi
India
;
_audit_update_record             
;
2024-09-13 deposited with the CCDC.	2024-11-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C4 H O4, C3 H5 N2'
_chemical_formula_sum            'C7 H6 N2 O4'
_chemical_formula_weight         182.14

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   9.4017(11)
_cell_length_b                   10.9630(15)
_cell_length_c                   7.6527(9)
_cell_angle_alpha                90
_cell_angle_beta                 99.639(5)
_cell_angle_gamma                90
_cell_volume                     777.63(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    400(2)
_cell_measurement_reflns_used    6237
_cell_measurement_theta_min      2.20
_cell_measurement_theta_max      28.36

_exptl_crystal_description       Block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.556
_exptl_crystal_F_000             376
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.298
_exptl_crystal_size_mid          0.258
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.130
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      400(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   Microfocus
_diffrn_measurement_device_type  'Bruker APEX-III CMOS detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14013
_diffrn_reflns_av_unetI/netI     0.0134
_diffrn_reflns_av_R_equivalents  0.0223
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.878
_diffrn_reflns_theta_max         28.390
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.982
_reflns_number_total             1925
_reflns_number_gt                1602
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    'XSeed (Barbour 2017)'
_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)+(0.0677P)²+0.1519P] 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_number_reflns         1925
_refine_ls_number_parameters     142
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0539
_refine_ls_R_factor_gt           0.0461
_refine_ls_wR_factor_ref         0.1395
_refine_ls_wR_factor_gt          0.1321
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_restrained_S_all      1.071
_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
O1 O 1.02246(10) 0.87822(8) 0.18311(16) 0.0588(3) Uani 1 1 d . . . . .
O3 O 0.69617(11) 0.60774(9) 0.33426(18) 0.0672(4) Uani 1 1 d . . . . .
O4 O 1.01611(11) 0.59498(9) 0.21617(18) 0.0660(4) Uani 1 1 d . . . . .
O2 O 0.70496(12) 0.89996(10) 0.2986(2) 0.0746(4) Uani 1 1 d . . . . .
C3 C 0.78318(13) 0.68167(11) 0.29330(18) 0.0459(3) Uani 1 1 d . . . . .
C2 C 0.78634(14) 0.81773(11) 0.27767(19) 0.0480(3) Uani 1 1 d . . . . .
C4 C 0.92287(13) 0.67792(11) 0.24133(18) 0.0444(3) Uani 1 1 d . . . . .
C1 C 0.93046(13) 0.80588(11) 0.22480(18) 0.0440(3) Uani 1 1 d . . . . .
N1 N 0.45409(14) 0.70936(14) 0.4437(2) 0.0622(4) Uani 1 1 d . . . . .
N2 N 0.25542(14) 0.71539(14) 0.54093(19) 0.0627(4) Uani 1 1 d . . . . .
C5 C 0.42272(19) 0.82790(16) 0.4635(3) 0.0675(5) Uani 1 1 d . . . . .
C7 C 0.35048(18) 0.64293(17) 0.4909(2) 0.0671(5) Uani 1 1 d . . . . .
C6 C 0.29755(19) 0.83209(17) 0.5246(2) 0.0673(5) Uani 1 1 d . . . . .
H4 H 0.9918(19) 0.516(2) 0.256(2) 0.102(8) Uiso 1 1 d . . . . .
H2 H 0.170(3) 0.691(2) 0.583(3) 0.107(7) Uiso 1 1 d . . . . .
H1 H 0.535(2) 0.679(2) 0.404(3) 0.098(7) Uiso 1 1 d . . . . .
H7 H 0.345(2) 0.554(3) 0.491(3) 0.126(9) Uiso 1 1 d . . . . .
H6 H 0.248(2) 0.896(2) 0.550(3) 0.100(7) Uiso 1 1 d . . . . .
H5 H 0.480(2) 0.887(2) 0.435(3) 0.094(7) 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 C1 1.2535(14) . ?
O3 C3 1.2290(15) . ?
O4 C4 1.2996(14) . ?
O2 C2 1.2103(15) . ?
C3 C4 1.4351(16) . ?
C3 C2 1.4970(18) . ?
C2 C1 1.4833(17) . ?
C4 C1 1.4114(17) . ?
N1 C7 1.314(2) . ?
N1 C5 1.347(2) . ?
N2 C7 1.300(2) . ?
N2 C6 1.351(2) . ?
C5 C6 1.338(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
O3 C3 C4 136.96(12) . . ?
O3 C3 C2 134.47(11) . . ?
C4 C3 C2 88.57(9) . . ?
O2 C2 C1 136.71(12) . . ?
O2 C2 C3 135.24(12) . . ?
C1 C2 C3 88.04(9) . . ?
O4 C4 C1 129.54(11) . . ?
O4 C4 C3 137.09(11) . . ?
C1 C4 C3 93.37(9) . . ?
O1 C1 C4 134.36(11) . . ?
O1 C1 C2 135.63(11) . . ?
C4 C1 C2 90.02(9) . . ?
C7 N1 C5 108.51(14) . . ?
C7 N2 C6 108.93(14) . . ?
C6 C5 N1 107.12(14) . . ?
N2 C7 N1 108.66(16) . . ?
C5 C6 N2 106.76(15) . . ?

_refine_diff_density_max         0.270
_refine_diff_density_min         -0.152
_refine_diff_density_rms         0.030



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Mixture of Methanol and Water'
####################################################################### 
# 
# 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_SQIM450K_HT
_database_code_depnum_ccdc_archive 'CCDC 2383789'
loop_
_audit_author_name
_audit_author_address
'Dinabandhu Das'
;Jawaharlal Nehru University, New Delhi
India
;
_audit_update_record             
;
2024-09-13 deposited with the CCDC.	2024-11-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C4 H O4, C3 H5 N2'
_chemical_formula_sum            'C7 H6 N2 O4'
_chemical_formula_weight         182.14

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   9.4270(12)
_cell_length_b                   10.9529(16)
_cell_length_c                   7.6965(10)
_cell_angle_alpha                90
_cell_angle_beta                 99.340(5)
_cell_angle_gamma                90
_cell_volume                     784.15(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    450(2)
_cell_measurement_reflns_used    5076
_cell_measurement_theta_min      2.19
_cell_measurement_theta_max      28.12

_exptl_crystal_description       Block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.543
_exptl_crystal_F_000             376
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.298
_exptl_crystal_size_mid          0.258
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.129
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.7006
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      450(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   Microfocus
_diffrn_measurement_device_type  'Bruker APEX-III CMOS detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14226
_diffrn_reflns_av_unetI/netI     0.0156
_diffrn_reflns_av_R_equivalents  0.0254
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.873
_diffrn_reflns_theta_max         28.405
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.984
_reflns_number_total             1941
_reflns_number_gt                1482
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    'XSeed (Barbour 2017)'
_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)+(0.0784P)²+0.1247P] 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_number_reflns         1941
_refine_ls_number_parameters     142
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0650
_refine_ls_R_factor_gt           0.0519
_refine_ls_wR_factor_ref         0.1610
_refine_ls_wR_factor_gt          0.1509
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_restrained_S_all      1.084
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 1.02204(11) 0.87905(9) 0.18592(19) 0.0696(4) Uani 1 1 d . . . . .
O3 O 0.69687(13) 0.60694(11) 0.3337(2) 0.0804(4) Uani 1 1 d . . . . .
O4 O 1.01653(13) 0.59586(10) 0.2168(2) 0.0770(4) Uani 1 1 d . . . . .
O2 O 0.70479(14) 0.89940(11) 0.3009(2) 0.0882(5) Uani 1 1 d . . . . .
C3 C 0.78358(15) 0.68138(13) 0.2939(2) 0.0544(4) Uani 1 1 d . . . . .
C2 C 0.78641(15) 0.81733(13) 0.2793(2) 0.0567(4) Uani 1 1 d . . . . .
C4 C 0.92327(15) 0.67843(12) 0.2423(2) 0.0521(4) Uani 1 1 d . . . . .
C1 C 0.93030(15) 0.80627(12) 0.2268(2) 0.0518(4) Uani 1 1 d . . . . .
N1 N 0.45354(17) 0.70912(17) 0.4446(2) 0.0758(5) Uani 1 1 d . . . . .
N2 N 0.25597(17) 0.71545(18) 0.5414(2) 0.0773(5) Uani 1 1 d . . . . .
C5 C 0.4227(2) 0.8267(2) 0.4636(3) 0.0830(6) Uani 1 1 d . . . . .
C7 C 0.3496(2) 0.6431(2) 0.4917(3) 0.0814(6) Uani 1 1 d . . . . .
C6 C 0.2977(2) 0.8315(2) 0.5251(3) 0.0818(6) Uani 1 1 d D . . . .
H1 H 0.537(3) 0.678(3) 0.402(4) 0.129(9) Uiso 1 1 d . . . . .
H5 H 0.479(3) 0.883(2) 0.434(3) 0.114(8) Uiso 1 1 d . . . . .
H2 H 0.165(3) 0.691(3) 0.583(4) 0.129(9) Uiso 1 1 d . . . . .
H7 H 0.345(3) 0.550(4) 0.498(4) 0.174(13) Uiso 1 1 d . . . . .
H6 H 0.248(2) 0.8985(19) 0.554(3) 0.124(9) Uiso 1 1 d D . . . .
H4 H 0.993(2) 0.515(2) 0.258(3) 0.115(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 C1 1.2533(16) . ?
O3 C3 1.2281(16) . ?
O4 C4 1.2983(16) . ?
O2 C2 1.2121(17) . ?
C3 C4 1.4362(18) . ?
C3 C2 1.494(2) . ?
C2 C1 1.4819(18) . ?
C4 C1 1.4078(19) . ?
N1 C7 1.315(2) . ?
N1 C5 1.334(3) . ?
N2 C7 1.290(3) . ?
N2 C6 1.343(3) . ?
C5 C6 1.341(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
O3 C3 C4 137.01(13) . . ?
O3 C3 C2 134.52(12) . . ?
C4 C3 C2 88.47(10) . . ?
O2 C2 C1 136.68(13) . . ?
O2 C2 C3 135.20(13) . . ?
C1 C2 C3 88.13(10) . . ?
O4 C4 C1 129.62(12) . . ?
O4 C4 C3 137.00(12) . . ?
C1 C4 C3 93.38(10) . . ?
O1 C1 C4 134.25(12) . . ?
O1 C1 C2 135.72(12) . . ?
C4 C1 C2 90.02(10) . . ?
C7 N1 C5 108.40(17) . . ?
C7 N2 C6 109.21(17) . . ?
N1 C5 C6 107.22(17) . . ?
N2 C7 N1 108.68(19) . . ?
C5 C6 N2 106.48(17) . . ?

_refine_diff_density_max         0.233
_refine_diff_density_min         -0.158
_refine_diff_density_rms         0.031



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Mixture of Methanol and Water'
