# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2022

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_2
_database_code_depnum_ccdc_archive 'CCDC 2048891'
loop_
_audit_author_name
_audit_author_address
'Chandra Shekhar Purohit'
;National Institute of Science Education and Research, Bhubaneswar
India
;
_audit_update_record             
;
2020-12-07 deposited with the CCDC.	2022-09-21 downloaded from the CCDC.
;
_audit_creation_date             2020-12-07
_audit_creation_method           
;
Olex2 1.3
(compiled Sep 10 2019 10:52:38 for OlexSys, GUI svn.r5938)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
Ethyl-6-fluoro-3-hydroxypyrazine-2-carboxylate
_chemical_formula_moiety         'C7 H7 F N2 O3'
_chemical_formula_sum            'C7 H7 F N2 O3'
_chemical_formula_weight         186.15
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C48 H32 F16 N24 O16 '
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   20.2620(5)
_cell_length_b                   4.72480(10)
_cell_length_c                   16.6253(4)
_cell_angle_alpha                90
_cell_angle_beta                 90.480(2)
_cell_angle_gamma                90
_cell_volume                     1591.55(6)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2953
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      76.6600
_cell_measurement_theta_min      6.8580
_shelx_estimated_absorpt_T_max   0.889
_shelx_estimated_absorpt_T_min   0.585
_exptl_absorpt_coefficient_mu    1.201
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.51138
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.63a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.554
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             768
_exptl_crystal_preparation       'AS PER MENTIONED IN PAPER'
_exptl_crystal_recrystallization_method 'SLOW EVAPORATION'
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0227
_diffrn_reflns_av_unetI/netI     0.0298
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            3860
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.482
_diffrn_reflns_theta_min         5.321
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.958
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -73.00 -25.00   0.50    0.50    --  -38.50  96.00 106.00   96
  2  ω    -22.00  19.00   0.50    0.50    --  -38.50  96.00 106.00   82
  3  ω      7.00  42.00   0.50    0.50    --   48.56 -96.00  -3.00   70
  4  ω    139.00 169.00   0.50    0.75    --  106.21  96.00 106.00   60
  5  ω   -101.00 -50.00   0.50    0.50    --  -38.50 -57.00  30.00  102
  6  ω    -11.00  20.00   0.50    0.50    --   48.56 -57.00-120.00   62
  7  ω     87.00 112.00   0.50    0.50    --   48.56  57.00-180.00   50
  8  ω     28.00  59.00   0.50    0.50    --   48.56 -57.00-120.00   62
  9  ω    104.00 169.00   0.50    0.75    --  106.21  77.00 -60.00  130
 10  ω     94.00 168.00   0.50    0.75    --  106.21  61.00   0.00  148
 11  ω    103.00 157.00   0.50    0.75    --  106.21  15.00-180.00  108
 12  ω     37.00 104.00   0.50    0.75    --  106.21-111.00 150.00  134
 13  ω     40.00  93.00   0.50    0.75    --  106.21 -94.00 -90.00  106
 14  ω     57.00 109.00   0.50    0.75    --  106.21-111.00-120.00  104
 15  ω     38.00  63.00   0.50    0.75    --  106.21 -94.00-120.00   50
 16  ω     42.00  81.00   0.50    0.75    --  106.21 -45.00 120.00   78
 17  ω    109.00 134.00   0.50    0.75    --  106.21  77.00-150.00   50
 18  ω     71.00 100.00   0.50    0.75    --  106.21 -94.00 -60.00   58
 19  ω     79.00 104.00   0.50    0.75    --  106.21 -96.00  -3.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'SuperNova, Dual, Cu at home/near, Pilatus 200K'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0441189000
_diffrn_orient_matrix_UB_12      -0.1280093000
_diffrn_orient_matrix_UB_13      0.0665637000
_diffrn_orient_matrix_UB_21      0.0556861000
_diffrn_orient_matrix_UB_22      0.2070286000
_diffrn_orient_matrix_UB_23      -0.0223087000
_diffrn_orient_matrix_UB_31      -0.0270401000
_diffrn_orient_matrix_UB_32      0.2170699000
_diffrn_orient_matrix_UB_33      0.0604848000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1477
_reflns_number_total             1614
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.248
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     120
_refine_ls_number_reflns         1614
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0401
_refine_ls_R_factor_gt           0.0374
_refine_ls_restrained_S_all      1.073
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0543P)²+1.0509P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0997
_refine_ls_wR_factor_ref         0.1022
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3)
2.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.43960(4) -0.19984(18) 0.30480(5) 0.0256(2) Uani 1 1 d . . . . .
O1 O 0.22955(4) 0.3813(2) 0.40176(6) 0.0202(2) Uani 1 1 d . . . . .
H1 H 0.239702 0.507351 0.433442 0.030 Uiso 1 1 calc R U . . .
O2 O 0.31414(4) 0.67164(19) 0.49397(5) 0.0196(2) Uani 1 1 d . . . . .
O3 O 0.41959(4) 0.5239(2) 0.50048(5) 0.0191(2) Uani 1 1 d . . . . .
N1 N 0.39933(5) 0.1416(2) 0.38580(6) 0.0171(3) Uani 1 1 d . . . . .
N2 N 0.27322(5) 0.0431(2) 0.32342(6) 0.0184(3) Uani 1 1 d . . . . .
C1 C 0.34729(6) 0.2915(3) 0.41153(7) 0.0157(3) Uani 1 1 d . . . . .
C2 C 0.28356(6) 0.2417(3) 0.37985(7) 0.0161(3) Uani 1 1 d . . . . .
C3 C 0.32507(6) -0.1024(3) 0.29823(8) 0.0192(3) Uani 1 1 d . . . . .
H3 H 0.319937 -0.240512 0.258824 0.023 Uiso 1 1 calc R U . . .
C4 C 0.38732(6) -0.0475(3) 0.33107(7) 0.0181(3) Uani 1 1 d . . . . .
C5 C 0.35836(6) 0.5143(3) 0.47334(7) 0.0155(3) Uani 1 1 d . . . . .
C6 C 0.43460(6) 0.7402(3) 0.56148(7) 0.0203(3) Uani 1 1 d . . . . .
H6A H 0.408904 0.909280 0.550566 0.024 Uiso 1 1 calc R U . . .
H6B H 0.480991 0.789989 0.559129 0.024 Uiso 1 1 calc R U . . .
C7 C 0.41867(8) 0.6303(4) 0.64400(8) 0.0316(4) Uani 1 1 d . . . . .
H7A H 0.371890 0.602702 0.648233 0.047 Uiso 1 1 calc R U . . .
H7B H 0.433046 0.764684 0.683750 0.047 Uiso 1 1 calc R U . . .
H7C H 0.440914 0.453360 0.652663 0.047 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C4 1.3561(15) . ?
O1 H1 0.8200 . ?
O1 C2 1.3313(15) . ?
O2 C5 1.2158(16) . ?
O3 C5 1.3174(15) . ?
O3 C6 1.4699(14) . ?
N1 C1 1.3431(17) . ?
N1 C4 1.2968(17) . ?
N2 C2 1.3420(16) . ?
N2 C3 1.3263(17) . ?
C1 C2 1.4103(17) . ?
C1 C5 1.4867(17) . ?
C3 H3 0.9300 . ?
C3 C4 1.3944(18) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C7 1.504(2) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 H1 109.5 . . ?
C5 O3 C6 116.69(9) . . ?
C4 N1 C1 116.33(11) . . ?
C3 N2 C2 117.62(11) . . ?
N1 C1 C2 120.79(11) . . ?
N1 C1 C5 118.64(11) . . ?
C2 C1 C5 120.57(11) . . ?
O1 C2 N2 114.45(11) . . ?
O1 C2 C1 124.56(11) . . ?
N2 C2 C1 120.99(12) . . ?
N2 C3 H3 120.1 . . ?
N2 C3 C4 119.75(12) . . ?
C4 C3 H3 120.1 . . ?
F1 C4 C3 118.79(11) . . ?
N1 C4 F1 116.68(11) . . ?
N1 C4 C3 124.53(12) . . ?
O2 C5 O3 125.21(11) . . ?
O2 C5 C1 121.38(11) . . ?
O3 C5 C1 113.40(10) . . ?
O3 C6 H6A 109.6 . . ?
O3 C6 H6B 109.6 . . ?
O3 C6 C7 110.15(11) . . ?
H6A C6 H6B 108.1 . . ?
C7 C6 H6A 109.6 . . ?
C7 C6 H6B 109.6 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 O1 -179.70(11) . . . . ?
N1 C1 C2 N2 0.17(19) . . . . ?
N1 C1 C5 O2 173.90(11) . . . . ?
N1 C1 C5 O3 -4.74(16) . . . . ?
N2 C3 C4 F1 179.61(11) . . . . ?
N2 C3 C4 N1 -0.4(2) . . . . ?
C1 N1 C4 F1 -179.96(10) . . . . ?
C1 N1 C4 C3 0.05(19) . . . . ?
C2 N2 C3 C4 0.61(18) . . . . ?
C2 C1 C5 O2 -5.22(19) . . . . ?
C2 C1 C5 O3 176.13(11) . . . . ?
C3 N2 C2 O1 179.38(11) . . . . ?
C3 N2 C2 C1 -0.51(18) . . . . ?
C4 N1 C1 C2 0.06(18) . . . . ?
C4 N1 C1 C5 -179.07(10) . . . . ?
C5 O3 C6 C7 85.71(13) . . . . ?
C5 C1 C2 O1 -0.59(19) . . . . ?
C5 C1 C2 N2 179.28(11) . . . . ?
C6 O3 C5 O2 1.03(18) . . . . ?
C6 O3 C5 C1 179.61(10) . . . . ?

_olex2_exptl_crystal_mounting_method 'MOUNTED ON LOOP'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.701
_oxdiff_exptl_absorpt_empirical_full_min 0.444
####################################################################### 
# 
# 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_3
_database_code_depnum_ccdc_archive 'CCDC 2048895'
loop_
_audit_author_name
_audit_author_address
'Chandra Shekhar Purohit'
;National Institute of Science Education and Research, Bhubaneswar
India
;
_audit_update_record             
;
2020-12-07 deposited with the CCDC.	2022-09-21 downloaded from the CCDC.
;
_audit_creation_date             2020-12-07
_audit_creation_method           
;
Olex2 1.3
(compiled Sep 10 2019 10:52:38 for OlexSys, GUI svn.r5938)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        FAVIPIRAVIR
_chemical_formula_moiety         'C5 H4 F N3 O2'
_chemical_formula_sum            'C5 H4 F N3 O2'
_chemical_formula_weight         157.11
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C24 H16 F4 N8 O8 '
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   9.0668(5)
_cell_length_b                   14.8508(10)
_cell_length_c                   4.5755(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     616.09(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1919
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      74.5690
_cell_measurement_theta_min      5.9020
_shelx_estimated_absorpt_T_max   0.774
_shelx_estimated_absorpt_T_min   0.680
_exptl_absorpt_coefficient_mu    1.349
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.32759
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.63a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.694
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             320
_exptl_crystal_preparation       'AS PER PROCEDURE IN PAPER'
_exptl_crystal_recrystallization_method 'SLOW EVAPORATION'
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0819
_diffrn_reflns_av_unetI/netI     0.0533
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -4
_diffrn_reflns_number            4149
_diffrn_reflns_point_group_measured_fraction_full 0.905
_diffrn_reflns_point_group_measured_fraction_max 0.905
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.177
_diffrn_reflns_theta_min         5.717
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -78.00  11.00   0.50    0.57    --  -38.50 105.00-130.00  178
  2  ω     11.00  88.00   0.50    0.57    --   48.56-105.00 128.00  154
  3  ω     33.00 108.00   0.50    0.57    --  101.38-105.00 128.00  150
  4  ω    -50.00  24.00   0.50    0.57    --  -38.50  57.00  30.00  148
  5  ω     45.00 115.00   0.50    0.57    --   48.56  37.00 -30.00  140
  6  ω     33.00 107.00   0.50    0.57    --  101.38 -94.00 -60.00  148
  7  ω    103.00 166.00   0.50    0.57    --  101.38  77.00 120.00  126
  8  ω    104.00 171.00   0.50    0.57    --  101.38 111.00 -30.00  134
  9  ω     37.00 106.00   0.50    0.57    --  101.38 -45.00  90.00  138
 10  ω     33.00 105.00   0.50    0.57    --  101.38 -30.00-180.00  144
 11  ω     97.00 166.00   0.50    0.57    --  101.38  45.00 -30.00  138
 12  ω    103.00 166.00   0.50    0.57    --  101.38  77.00 -90.00  126
 13  ω    104.00 170.00   0.50    0.57    --  101.38 105.00-130.00  132
 14  ω     37.00 112.00   0.50    0.57    --   48.56  57.00  90.00  150
 15  ω     37.00 112.00   0.50    0.57    --   48.56  57.00 150.00  150
 16  ω     37.00 112.00   0.50    0.57    --   48.56  57.00  30.00  150
 17  ω     37.00 112.00   0.50    0.57    --   48.56  57.00-120.00  150
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'SuperNova, Dual, Cu at home/near, Pilatus 200K'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0356047000
_diffrn_orient_matrix_UB_12      0.1001304000
_diffrn_orient_matrix_UB_13      -0.0515197000
_diffrn_orient_matrix_UB_21      -0.1092335000
_diffrn_orient_matrix_UB_22      -0.0018497000
_diffrn_orient_matrix_UB_23      0.2579474000
_diffrn_orient_matrix_UB_31      0.1251357000
_diffrn_orient_matrix_UB_32      0.0268534000
_diffrn_orient_matrix_UB_33      0.2105568000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.605
_reflns_Friedel_fraction_full    0.787
_reflns_Friedel_fraction_max     0.787
_reflns_number_gt                881
_reflns_number_total             1027
_reflns_odcompleteness_completeness 99.71
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.248
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.067
_refine_ls_abs_structure_details 
;
 Flack x determined using 276 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.2(5)
_refine_ls_extinction_coef       0.005(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     102
_refine_ls_number_reflns         1027
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0691
_refine_ls_R_factor_gt           0.0586
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1030P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1412
_refine_ls_wR_factor_ref         0.1498
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3)
2.b X=CH2 refined with riding coordinates:
 N3(H3A,H3B)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F -0.4806(3) -0.93196(17) -0.2924(8) 0.0517(10) Uani 1 1 d . . . . .
O1 O -0.1986(3) -0.6650(2) -0.8226(8) 0.0421(10) Uani 1 1 d . . . . .
H1 H -0.227879 -0.614832 -0.761032 0.063 Uiso 1 1 calc R U . . .
O2 O -0.3519(3) -0.5564(2) -0.5039(8) 0.0363(9) Uani 1 1 d . . . . .
N1 N -0.4483(4) -0.7827(2) -0.3377(10) 0.0344(10) Uani 1 1 d . . . . .
N2 N -0.2381(4) -0.8142(3) -0.7705(9) 0.0373(10) Uani 1 1 d . . . . .
N3 N -0.5166(4) -0.6116(2) -0.1805(10) 0.0345(10) Uani 1 1 d . . . . .
H3A H -0.543525 -0.557354 -0.124161 0.041 Uiso 1 1 calc R U . . .
H3B H -0.557854 -0.659374 -0.101358 0.041 Uiso 1 1 calc R U . . .
C1 C -0.3777(5) -0.7144(3) -0.4703(11) 0.0302(11) Uani 1 1 d . . . . .
C2 C -0.2724(5) -0.7308(3) -0.6864(11) 0.0335(12) Uani 1 1 d . . . . .
C3 C -0.3085(5) -0.8810(3) -0.6382(13) 0.0397(13) Uani 1 1 d . . . . .
H3 H -0.287834 -0.941620 -0.690408 0.048 Uiso 1 1 calc R U . . .
C4 C -0.4122(5) -0.8624(3) -0.4238(12) 0.0367(13) Uani 1 1 d . . . . .
C5 C -0.4150(5) -0.6212(3) -0.3824(12) 0.0327(11) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C4 1.346(6) . ?
O1 H1 0.8400 . ?
O1 C2 1.338(5) . ?
O2 C5 1.250(6) . ?
N1 C1 1.344(6) . ?
N1 C4 1.290(6) . ?
N2 C2 1.334(6) . ?
N2 C3 1.326(6) . ?
N3 H3A 0.8800 . ?
N3 H3B 0.8800 . ?
N3 C5 1.312(7) . ?
C1 C2 1.396(7) . ?
C1 C5 1.480(6) . ?
C3 H3 0.9500 . ?
C3 C4 1.387(8) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 H1 109.5 . . ?
C4 N1 C1 115.7(4) . . ?
C3 N2 C2 116.8(4) . . ?
H3A N3 H3B 120.0 . . ?
C5 N3 H3A 120.0 . . ?
C5 N3 H3B 120.0 . . ?
N1 C1 C2 120.9(4) . . ?
N1 C1 C5 118.3(4) . . ?
C2 C1 C5 120.8(4) . . ?
O1 C2 C1 123.0(4) . . ?
N2 C2 O1 115.3(4) . . ?
N2 C2 C1 121.7(4) . . ?
N2 C3 H3 120.0 . . ?
N2 C3 C4 120.0(4) . . ?
C4 C3 H3 120.0 . . ?
F1 C4 C3 118.4(4) . . ?
N1 C4 F1 116.8(4) . . ?
N1 C4 C3 124.8(5) . . ?
O2 C5 N3 123.4(5) . . ?
O2 C5 C1 119.6(5) . . ?
N3 C5 C1 116.9(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 O1 -179.4(4) . . . . ?
N1 C1 C2 N2 0.3(7) . . . . ?
N1 C1 C5 O2 -179.4(4) . . . . ?
N1 C1 C5 N3 -0.6(6) . . . . ?
N2 C3 C4 F1 -179.5(5) . . . . ?
N2 C3 C4 N1 0.1(8) . . . . ?
C1 N1 C4 F1 179.5(4) . . . . ?
C1 N1 C4 C3 -0.1(7) . . . . ?
C2 N2 C3 C4 0.1(7) . . . . ?
C2 C1 C5 O2 0.3(7) . . . . ?
C2 C1 C5 N3 179.1(5) . . . . ?
C3 N2 C2 O1 179.5(4) . . . . ?
C3 N2 C2 C1 -0.2(7) . . . . ?
C4 N1 C1 C2 -0.1(7) . . . . ?
C4 N1 C1 C5 179.6(4) . . . . ?
C5 C1 C2 O1 0.9(7) . . . . ?
C5 C1 C2 N2 -179.4(5) . . . . ?

_olex2_exptl_crystal_mounting_method 'MOUNTED ON LOOP'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.070
_oxdiff_exptl_absorpt_empirical_full_min 0.617
####################################################################### 
# 
# 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_1a
_database_code_depnum_ccdc_archive 'CCDC 2048892'
loop_
_audit_author_name
_audit_author_address
'Chandra Shekhar Purohit'
;National Institute of Science Education and Research, Bhubaneswar
India
;
_audit_update_record             
;
2020-12-07 deposited with the CCDC.	2022-09-21 downloaded from the CCDC.
;
_audit_creation_date             2020-12-07
_audit_creation_method           
;
Olex2 1.3
(compiled Sep 10 2019 10:52:38 for OlexSys, GUI svn.r5938)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        Methyl-3-oxo-4-hydropyrazine-2-carboxylate
_chemical_formula_moiety         '2(C6 H6 N2 O3), 5(H2 O)'
_chemical_formula_sum            'C12 H22 N4 O11'
_chemical_formula_weight         398.33
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C88 H184 N40 O88 '
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   11.35633(17)
_cell_length_b                   12.7400(3)
_cell_length_c                   24.1766(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3497.87(12)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4288
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      76.5820
_cell_measurement_theta_min      5.5150
_shelx_estimated_absorpt_T_max   0.892
_shelx_estimated_absorpt_T_min   0.592
_exptl_absorpt_coefficient_mu    1.173
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64118
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.63a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.513
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1680
_exptl_crystal_preparation       'AS PER METHOD IN PAPER'
_exptl_crystal_recrystallization_method 'SLOW EVAPORATION'
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0520
_diffrn_reflns_av_unetI/netI     0.0502
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            13459
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.777
_diffrn_reflns_theta_min         3.656
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -54.00 -22.00   0.50    6.00    --  -38.50 108.00-105.00   64
  2  ω     28.00  53.00   0.50    6.00    --   48.56-108.00 156.00   50
  3  ω     42.00 108.00   0.50   10.00    --  106.21-108.00 156.00  132
  4  ω    113.00 142.00   0.50   10.00    --  106.21 108.00-105.00   58
  5  ω   -104.00 -37.00   0.50    6.00    --  -38.50 -37.00 150.00  134
  6  ω    -25.00  25.00   0.50    6.00    --  -38.50  37.00  90.00  100
  7  ω    -50.00   8.00   0.50    6.00    --  -38.50  57.00   0.00  116
  8  ω     61.00  86.00   0.50    6.00    --   48.56  37.00 -30.00   50
  9  ω    119.00 170.00   0.50   10.00    --  106.21  30.00-150.00  102
 10  ω     49.00 109.00   0.50   10.00    --  106.21 -45.00   0.00  120
 11  ω    106.00 142.00   0.50   10.00    --  106.21  77.00  60.00   72
 12  ω     44.00 103.00   0.50   10.00    --  106.21-111.00-120.00  118
 13  ω     38.00 106.00   0.50   10.00    --  106.21 -94.00 -30.00  136
 14  ω     48.00 110.00   0.50   10.00    --  106.21 -30.00 -90.00  124
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'SuperNova, Dual, Cu at home/near, Pilatus 200K'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0640319000
_diffrn_orient_matrix_UB_12      0.0077895000
_diffrn_orient_matrix_UB_13      -0.0560227000
_diffrn_orient_matrix_UB_21      0.1118654000
_diffrn_orient_matrix_UB_22      0.0466182000
_diffrn_orient_matrix_UB_23      -0.0263980000
_diffrn_orient_matrix_UB_31      0.0422619000
_diffrn_orient_matrix_UB_32      -0.1113429000
_diffrn_orient_matrix_UB_33      -0.0149384000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2937
_reflns_number_total             3611
_reflns_odcompleteness_completeness 99.84
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.379
_refine_diff_density_min         -0.306
_refine_diff_density_rms         0.069
_refine_ls_extinction_coef       0.00016(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     277
_refine_ls_number_reflns         3611
_refine_ls_number_restraints     15
_refine_ls_R_factor_all          0.0638
_refine_ls_R_factor_gt           0.0511
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0573P)²+2.5388P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1240
_refine_ls_wR_factor_ref         0.1316
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2. Restrained distances
 O8-H8A = O8-H8B
 0.85 with sigma of 0.02
 O7-H7A = O7-H7B
 0.85 with sigma of 0.02
 O9-H9A = O9-H9B
 0.85 with sigma of 0.02
 O10-H10A = O10-H10B
 0.85 with sigma of 0.02
 O11-H11A = O11-H11B
 0.85 with sigma of 0.02
 H10A-H10B
 1.34 with sigma of 0.04
 H7A-H7B
 1.34 with sigma of 0.04
 H8A-H8B
 1.34 with sigma of 0.04
 H9A-H9B
 1.34 with sigma of 0.04
 H11A-H11B
 1.34 with sigma of 0.04
3.a Aromatic/amide H refined with riding coordinates:
 N2(H2), C3(H3), C4(H4), N4(H4A), C9(H9), C10(H10)
3.b Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C12(H12A,H12B,H12C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.61165(12) 0.25283(12) 0.33302(6) 0.0249(3) Uani 1 1 d . . . . .
O2 O 0.98229(12) 0.27977(13) 0.35481(6) 0.0290(4) Uani 1 1 d . . . . .
O3 O 0.81013(11) 0.25570(11) 0.39803(5) 0.0212(3) Uani 1 1 d . . . . .
O7 O 0.55828(13) 0.19531(13) 0.44045(6) 0.0271(3) Uani 1 1 d D . . . .
H7A H 0.591(2) 0.206(2) 0.4101(8) 0.041 Uiso 1 1 d D U . . .
H7B H 0.597(2) 0.188(2) 0.4691(8) 0.041 Uiso 1 1 d D U . . .
N1 N 0.88241(14) 0.26037(12) 0.25599(7) 0.0190(3) Uani 1 1 d . . . . .
N2 N 0.64615(13) 0.25559(12) 0.24056(7) 0.0183(3) Uani 1 1 d . . . . .
H2 H 0.571511 0.254157 0.234594 0.022 Uiso 1 1 calc R U . . .
C1 C 0.81231(16) 0.25893(15) 0.29951(8) 0.0176(4) Uani 1 1 d . . . . .
C2 C 0.68387(16) 0.25485(15) 0.29489(8) 0.0185(4) Uani 1 1 d . . . . .
C3 C 0.71796(17) 0.25838(16) 0.19636(8) 0.0205(4) Uani 1 1 d . . . . .
H3 H 0.686965 0.259408 0.160754 0.025 Uiso 1 1 calc R U . . .
C4 C 0.83716(16) 0.25968(16) 0.20443(8) 0.0203(4) Uani 1 1 d . . . . .
H4 H 0.887465 0.260095 0.174075 0.024 Uiso 1 1 calc R U . . .
C5 C 0.87691(17) 0.26576(15) 0.35334(8) 0.0202(4) Uani 1 1 d . . . . .
C6 C 0.87320(18) 0.27212(18) 0.44957(9) 0.0262(5) Uani 1 1 d . . . . .
H6A H 0.909256 0.340272 0.449229 0.039 Uiso 1 1 calc R U . . .
H6B H 0.932916 0.219318 0.453542 0.039 Uiso 1 1 calc R U . . .
H6C H 0.819126 0.267621 0.479996 0.039 Uiso 1 1 calc R U . . .
O4 O 0.58608(12) 0.49488(11) 0.66745(6) 0.0229(3) Uani 1 1 d . . . . .
O5 O 0.21639(12) 0.51701(11) 0.64269(6) 0.0233(3) Uani 1 1 d . . . . .
O6 O 0.39267(11) 0.49231(11) 0.60244(6) 0.0216(3) Uani 1 1 d . . . . .
O10 O 0.65080(15) 0.36745(13) 0.57325(7) 0.0329(4) Uani 1 1 d D . . . .
H10A H 0.7140(19) 0.401(2) 0.5698(11) 0.049 Uiso 1 1 d D U . . .
H10B H 0.618(2) 0.401(2) 0.6006(9) 0.049 Uiso 1 1 d D U . . .
N3 N 0.31340(14) 0.49433(12) 0.74325(7) 0.0183(3) Uani 1 1 d . . . . .
N4 N 0.54996(14) 0.49200(12) 0.75958(7) 0.0180(3) Uani 1 1 d . . . . .
H4A H 0.624571 0.492138 0.765678 0.022 Uiso 1 1 calc R U . . .
C7 C 0.38445(16) 0.49619(14) 0.69997(8) 0.0171(4) Uani 1 1 d . . . . .
C8 C 0.51222(16) 0.49427(14) 0.70517(8) 0.0178(4) Uani 1 1 d . . . . .
C9 C 0.47721(16) 0.48958(15) 0.80367(8) 0.0184(4) Uani 1 1 d . . . . .
H9 H 0.507475 0.487533 0.839394 0.022 Uiso 1 1 calc R U . . .
C10 C 0.35748(17) 0.49019(15) 0.79492(8) 0.0197(4) Uani 1 1 d . . . . .
H10 H 0.306484 0.487727 0.824992 0.024 Uiso 1 1 calc R U . . .
C11 C 0.32179(16) 0.50331(15) 0.64564(8) 0.0194(4) Uani 1 1 d . . . . .
C12 C 0.33855(19) 0.50591(18) 0.54850(9) 0.0273(5) Uani 1 1 d . . . . .
H12A H 0.392396 0.483465 0.520272 0.041 Uiso 1 1 calc R U . . .
H12B H 0.319528 0.578604 0.543067 0.041 Uiso 1 1 calc R U . . .
H12C H 0.267932 0.464658 0.546509 0.041 Uiso 1 1 calc R U . . .
O8 O 0.66626(13) 0.15926(12) 0.54156(6) 0.0259(3) Uani 1 1 d D . . . .
H8A H 0.7385(16) 0.147(2) 0.5514(10) 0.039 Uiso 1 1 d D U . . .
H8B H 0.644(2) 0.2106(18) 0.5626(10) 0.039 Uiso 1 1 d D U . . .
O9 O 0.89701(13) 0.13818(12) 0.57189(7) 0.0286(4) Uani 1 1 d D . . . .
H9A H 0.946(2) 0.1879(18) 0.5703(11) 0.043 Uiso 1 1 d D U . . .
H9B H 0.915(2) 0.1012(19) 0.5993(9) 0.043 Uiso 1 1 d D U . . .
O11 O 0.87611(16) 0.45080(14) 0.57078(8) 0.0387(4) Uani 1 1 d D . . . .
H11A H 0.885(3) 0.5098(15) 0.5589(12) 0.058 Uiso 1 1 d D U . . .
H11B H 0.936(2) 0.414(2) 0.5658(13) 0.058 Uiso 1 1 d D U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.234(2) . ?
O2 C5 1.211(2) . ?
O3 C5 1.326(2) . ?
O3 C6 1.452(2) . ?
O7 H7A 0.834(16) . ?
O7 H7B 0.824(16) . ?
N1 C1 1.319(2) . ?
N1 C4 1.348(3) . ?
N2 H2 0.8600 . ?
N2 C2 1.382(3) . ?
N2 C3 1.345(2) . ?
C1 C2 1.464(2) . ?
C1 C5 1.496(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.368(3) . ?
C4 H4 0.9300 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
O4 C8 1.239(2) . ?
O5 C11 1.212(2) . ?
O6 C11 1.326(2) . ?
O6 C12 1.452(2) . ?
O10 H10A 0.838(17) . ?
O10 H10B 0.871(17) . ?
N3 C7 1.322(2) . ?
N3 C10 1.347(3) . ?
N4 H4A 0.8600 . ?
N4 C8 1.384(3) . ?
N4 C9 1.349(2) . ?
C7 C8 1.457(2) . ?
C7 C11 1.497(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.376(3) . ?
C10 H10 0.9300 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
O8 H8A 0.868(17) . ?
O8 H8B 0.865(17) . ?
O9 H9A 0.844(17) . ?
O9 H9B 0.838(16) . ?
O11 H11A 0.811(17) . ?
O11 H11B 0.838(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
C5 O3 C6 113.76(15) . . ?
H7A O7 H7B 121(3) . . ?
C1 N1 C4 120.48(16) . . ?
C2 N2 H2 117.7 . . ?
C3 N2 H2 117.7 . . ?
C3 N2 C2 124.59(16) . . ?
N1 C1 C2 122.73(18) . . ?
N1 C1 C5 113.39(16) . . ?
C2 C1 C5 123.85(17) . . ?
O1 C2 N2 120.28(17) . . ?
O1 C2 C1 127.29(18) . . ?
N2 C2 C1 112.42(16) . . ?
N2 C3 H3 120.4 . . ?
N2 C3 C4 119.15(18) . . ?
C4 C3 H3 120.4 . . ?
N1 C4 C3 120.61(18) . . ?
N1 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
O2 C5 O3 123.76(18) . . ?
O2 C5 C1 121.25(18) . . ?
O3 C5 C1 114.99(16) . . ?
O3 C6 H6A 109.5 . . ?
O3 C6 H6B 109.5 . . ?
O3 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C11 O6 C12 115.96(15) . . ?
H10A O10 H10B 102(2) . . ?
C7 N3 C10 120.54(16) . . ?
C8 N4 H4A 117.9 . . ?
C9 N4 H4A 117.9 . . ?
C9 N4 C8 124.18(16) . . ?
N3 C7 C8 122.65(17) . . ?
N3 C7 C11 113.93(16) . . ?
C8 C7 C11 123.40(17) . . ?
O4 C8 N4 119.35(17) . . ?
O4 C8 C7 127.63(18) . . ?
N4 C8 C7 113.02(16) . . ?
N4 C9 H9 120.5 . . ?
N4 C9 C10 118.93(18) . . ?
C10 C9 H9 120.5 . . ?
N3 C10 C9 120.67(18) . . ?
N3 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
O5 C11 O6 124.65(18) . . ?
O5 C11 C7 122.01(18) . . ?
O6 C11 C7 113.34(16) . . ?
O6 C12 H12A 109.5 . . ?
O6 C12 H12B 109.5 . . ?
O6 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
H8A O8 H8B 104(2) . . ?
H9A O9 H9B 107(2) . . ?
H11A O11 H11B 112(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 O1 179.68(19) . . . . ?
N1 C1 C2 N2 -1.6(3) . . . . ?
N1 C1 C5 O2 5.6(3) . . . . ?
N1 C1 C5 O3 -174.61(16) . . . . ?
N2 C3 C4 N1 -1.4(3) . . . . ?
C1 N1 C4 C3 0.6(3) . . . . ?
C2 N2 C3 C4 0.6(3) . . . . ?
C2 C1 C5 O2 -172.31(19) . . . . ?
C2 C1 C5 O3 7.5(3) . . . . ?
C3 N2 C2 O1 179.59(18) . . . . ?
C3 N2 C2 C1 0.8(3) . . . . ?
C4 N1 C1 C2 1.0(3) . . . . ?
C4 N1 C1 C5 -176.92(17) . . . . ?
C5 C1 C2 O1 -2.6(3) . . . . ?
C5 C1 C2 N2 176.09(16) . . . . ?
C6 O3 C5 O2 5.1(3) . . . . ?
C6 O3 C5 C1 -174.71(16) . . . . ?
N3 C7 C8 O4 179.36(18) . . . . ?
N3 C7 C8 N4 -0.9(3) . . . . ?
N3 C7 C11 O5 7.2(3) . . . . ?
N3 C7 C11 O6 -172.28(16) . . . . ?
N4 C9 C10 N3 -0.7(3) . . . . ?
C7 N3 C10 C9 1.1(3) . . . . ?
C8 N4 C9 C10 -0.5(3) . . . . ?
C8 C7 C11 O5 -171.26(18) . . . . ?
C8 C7 C11 O6 9.3(3) . . . . ?
C9 N4 C8 O4 -178.97(17) . . . . ?
C9 N4 C8 C7 1.3(3) . . . . ?
C10 N3 C7 C8 -0.2(3) . . . . ?
C10 N3 C7 C11 -178.65(16) . . . . ?
C11 C7 C8 O4 -2.3(3) . . . . ?
C11 C7 C8 N4 177.37(16) . . . . ?
C12 O6 C11 O5 4.8(3) . . . . ?
C12 O6 C11 C7 -175.77(16) . . . . ?

_olex2_exptl_crystal_mounting_method 'MOUNTED ON LOOP'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.557
_oxdiff_exptl_absorpt_empirical_full_min 0.542
####################################################################### 
# 
# 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_4
_database_code_depnum_ccdc_archive 'CCDC 2155451'
loop_
_audit_author_name
_audit_author_address
'Priyanka Ghosh'
;NISER, HBNI
India
;
_audit_update_record             
;
2022-02-28 deposited with the CCDC.	2022-09-21 downloaded from the CCDC.
;
_audit_creation_date             2022-02-28
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C7 H7 Cl N2 O3.014)'
_chemical_formula_sum            'C14 H14 Cl2 N4 O6'
_chemical_formula_weight         405.19
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C56 H56 Cl8 N16 O24 '
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      tetragonal
_space_group_IT_number           86
_space_group_name_H-M_alt        'P 42/n'
_space_group_name_Hall           '-P 4bc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z'
'-y, x+1/2, z+1/2'
'y+1/2, -x, z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'y, -x-1/2, -z-1/2'
'-y-1/2, x, -z-1/2'

_cell_length_a                   18.7318(5)
_cell_length_b                   18.7318(5)
_cell_length_c                   5.1839(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1818.93(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2607
_cell_measurement_temperature    300(1)
_cell_measurement_theta_max      74.0730
_cell_measurement_theta_min      4.7120
_shelx_estimated_absorpt_T_max   0.634
_shelx_estimated_absorpt_T_min   0.445
_exptl_absorpt_coefficient_mu    3.577
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.480
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             832
_exptl_crystal_preparation       'As per the reaction scheme'
_exptl_crystal_recrystallization_method 'Slow evapration'
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0384
_diffrn_reflns_av_unetI/netI     0.0300
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -4
_diffrn_reflns_number            7563
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.310
_diffrn_reflns_theta_min         4.721
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      300(1)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.9978
_diffrn_measured_fraction_theta_max 0.9778
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -77.00  14.00   0.50    2.00    --  -38.50 104.00  28.00  182
  2  ω    104.00 171.00   0.50    8.00    --  102.63 104.00  28.00  134
  3  ω     34.00 107.00   0.50    8.00    --  102.63-104.00 -72.00  146
  4  ω   -101.00 -27.00   0.50    2.00    --  -38.50 -57.00-150.00  148
  5  ω      7.00  88.00   0.50    2.00    --   49.31-104.00 -72.00  162
  6  ω     46.00 116.00   0.50    2.00    --   49.31  38.00 120.00  140
  7  ω     38.00 107.00   0.50    8.00    --  102.63 -45.00 -30.00  138
  8  ω    125.00 168.00   0.50    8.00    --  102.63 125.00 -60.00   86
  9  ω    123.00 148.00   0.50    8.00    --  102.63  77.00-150.00   50
 10  ω     95.00 171.00   0.50    8.00    --  102.63  15.00-150.00  152
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'SuperNova, Dual, Cu at home/near, Pilatus 200K'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0746278000
_diffrn_orient_matrix_UB_12      -0.0290093000
_diffrn_orient_matrix_UB_13      0.0702549000
_diffrn_orient_matrix_UB_21      0.0273865000
_diffrn_orient_matrix_UB_22      -0.0769338000
_diffrn_orient_matrix_UB_23      -0.0317331000
_diffrn_orient_matrix_UB_31      0.0210472000
_diffrn_orient_matrix_UB_32      -0.0014366000
_diffrn_orient_matrix_UB_33      0.2870723000
_diffrn_oxdiff_digest_frames     
;
0198e203fe803829c5675960c548fe55030003042ca
;
_diffrn_oxdiff_digest_hkl        
;
01d2c7e1d33a59487d4b81091c80f988a6f06e
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1506
_reflns_number_total             1850
_reflns_odcompleteness_completeness 99.78
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.193
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     131
_refine_ls_number_reflns         1850
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0481
_refine_ls_R_factor_gt           0.0389
_refine_ls_restrained_S_all      1.055
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0558P)²+0.3289P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1095
_refine_ls_wR_factor_ref         0.1162
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4)
2.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.68039(4) 0.82365(3) 1.03549(12) 0.0866(3) Uani 1 1 d . . . . .
O1 O 0.60123(9) 1.02721(8) 0.2692(3) 0.0812(5) Uani 1 1 d . . . . .
H1 H 0.566445 1.014035 0.185781 0.122 Uiso 1 1 calc R U . . .
O3 O 0.48129(8) 0.84087(7) 0.3913(3) 0.0731(4) Uani 1 1 d . . . . .
N1 N 0.67582(10) 0.99211(10) 0.5816(4) 0.0772(5) Uani 1 1 d . . . . .
N2 N 0.59717(8) 0.86861(8) 0.6687(3) 0.0548(4) Uani 1 1 d . . . . .
C1 C 0.61762(11) 0.97769(10) 0.4451(4) 0.0607(5) Uani 1 1 d . . . . .
C2 C 0.57791(10) 0.91583(9) 0.4875(3) 0.0526(4) Uani 1 1 d . . . . .
C3 C 0.65470(10) 0.88388(11) 0.7999(4) 0.0610(5) Uani 1 1 d . . . . .
C4 C 0.69445(12) 0.94497(12) 0.7585(5) 0.0756(6) Uani 1 1 d . . . . .
H4 H 0.735109 0.953031 0.857262 0.091 Uiso 1 1 calc R U . . .
C5 C 0.51330(10) 0.90058(10) 0.3322(4) 0.0593(5) Uani 1 1 d . . . . .
C6 C 0.41552(14) 0.82467(14) 0.2518(6) 0.0986(9) Uani 1 1 d . . . . .
H6A H 0.386870 0.867509 0.233460 0.118 Uiso 1 1 calc R U . . .
H6B H 0.426622 0.806726 0.080881 0.118 Uiso 1 1 calc R U . . .
C7 C 0.37633(17) 0.7709(2) 0.3982(9) 0.1287(13) Uani 1 1 d . . . . .
H7A H 0.331124 0.762133 0.316841 0.193 Uiso 1 1 calc R U . . .
H7B H 0.368638 0.787746 0.570833 0.193 Uiso 1 1 calc R U . . .
H7C H 0.403435 0.727420 0.403124 0.193 Uiso 1 1 calc R U . . .
O5 O 0.4997(17) 0.9366(14) 0.142(5) 0.070(3) Uani 0.47(7) 1 d . . . A 1
O4 O 0.4875(11) 0.9458(13) 0.189(5) 0.069(3) Uani 0.54(7) 1 d . . . A -1


_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
Cl1 C3 1.7310(19) . ?
O1 H1 0.8200 . ?
O1 C1 1.336(2) . ?
O3 C5 1.306(2) . ?
O3 C6 1.460(3) . ?
N1 C1 1.328(3) . ?
N1 C4 1.320(3) . ?
N2 C2 1.340(2) . ?
N2 C3 1.306(2) . ?
C1 C2 1.395(3) . ?
C2 C5 1.481(2) . ?
C3 C4 1.382(3) . ?
C4 H4 0.9300 . ?
C5 O5 1.22(2) . ?
C5 O4 1.22(2) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C7 1.459(4) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?

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
C1 O1 H1 109.5 . . ?
C5 O3 C6 116.69(16) . . ?
C4 N1 C1 116.84(18) . . ?
C3 N2 C2 116.28(16) . . ?
O1 C1 C2 124.18(18) . . ?
N1 C1 O1 114.29(18) . . ?
N1 C1 C2 121.53(17) . . ?
N2 C2 C1 121.03(17) . . ?
N2 C2 C5 118.29(16) . . ?
C1 C2 C5 120.68(16) . . ?
N2 C3 Cl1 117.00(15) . . ?
N2 C3 C4 123.04(18) . . ?
C4 C3 Cl1 119.96(15) . . ?
N1 C4 C3 121.28(19) . . ?
N1 C4 H4 119.4 . . ?
C3 C4 H4 119.4 . . ?
O3 C5 C2 114.38(15) . . ?
O5 C5 O3 124.5(12) . . ?
O5 C5 C2 120.2(13) . . ?
O5 C5 O4 17.7(14) . . ?
O4 C5 O3 123.6(10) . . ?
O4 C5 C2 121.1(11) . . ?
O3 C6 H6A 110.1 . . ?
O3 C6 H6B 110.1 . . ?
H6A C6 H6B 108.4 . . ?
C7 C6 O3 108.1(2) . . ?
C7 C6 H6A 110.1 . . ?
C7 C6 H6B 110.1 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cl1 C3 C4 N1 -179.46(18) . . . . ?
O1 C1 C2 N2 -179.51(18) . . . . ?
O1 C1 C2 C5 0.7(3) . . . . ?
N1 C1 C2 N2 0.1(3) . . . . ?
N1 C1 C2 C5 -179.72(19) . . . . ?
N2 C2 C5 O3 0.0(3) . . . . ?
N2 C2 C5 O5 -169.5(18) . . . . ?
N2 C2 C5 O4 169.9(16) . . . . ?
N2 C3 C4 N1 0.3(4) . . . . ?
C1 N1 C4 C3 -0.5(3) . . . . ?
C1 C2 C5 O3 179.83(18) . . . . ?
C1 C2 C5 O5 10.3(18) . . . . ?
C1 C2 C5 O4 -10.3(16) . . . . ?
C2 N2 C3 Cl1 179.85(13) . . . . ?
C2 N2 C3 C4 0.1(3) . . . . ?
C3 N2 C2 C1 -0.3(3) . . . . ?
C3 N2 C2 C5 179.52(17) . . . . ?
C4 N1 C1 O1 179.9(2) . . . . ?
C4 N1 C1 C2 0.3(3) . . . . ?
C5 O3 C6 C7 -161.4(3) . . . . ?
C6 O3 C5 C2 177.4(2) . . . . ?
C6 O3 C5 O5 -14(2) . . . . ?
C6 O3 C5 O4 7.9(17) . . . . ?

_olex2_exptl_crystal_mounting_method 'Mounted on the loop'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.671
_oxdiff_exptl_absorpt_empirical_full_min 0.533
####################################################################### 
# 
# 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_5
_database_code_depnum_ccdc_archive 'CCDC 2155453'
loop_
_audit_author_name
_audit_author_address
'Priyanka Ghosh'
;NISER, HBNI
India
;
_audit_update_record             
;
2022-02-28 deposited with the CCDC.	2022-09-21 downloaded from the CCDC.
;
_audit_creation_date             2022-02-28
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C5 H4 Br N3 O2'
_chemical_formula_sum            'C5 H4 Br N3 O2'
_chemical_formula_weight         218.02
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C18 I2 N10 O6 '
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   4.26356(16)
_cell_length_b                   5.3334(2)
_cell_length_c                   15.8471(6)
_cell_angle_alpha                90
_cell_angle_beta                 93.394(4)
_cell_angle_gamma                90
_cell_volume                     359.72(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3253
_cell_measurement_temperature    157(30)
_cell_measurement_theta_max      74.4320
_cell_measurement_theta_min      5.5830
_shelx_estimated_absorpt_T_max   0.422
_shelx_estimated_absorpt_T_min   0.214
_exptl_absorpt_coefficient_mu    7.439
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.38759
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    2.013
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             212
_exptl_crystal_preparation       'As per the reaction scheme'
_exptl_crystal_recrystallization_method 'Slow evaporation'
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0391
_diffrn_reflns_av_unetI/netI     0.0269
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            5212
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.106
_diffrn_reflns_theta_min         5.593
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      157(30)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.9986
_diffrn_measured_fraction_theta_max 0.9687
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -65.00  28.00   0.50    0.30    --  -38.50  82.00 -18.00  186
  2  ω    -17.00  76.00   0.50    0.30    --   49.31 -82.00-140.00  186
  3  ω     37.00 129.00   0.50    1.11    --  102.63 -82.00-140.00  184
  4  ω    103.00 169.00   0.50    1.11    --  102.63  82.00 -18.00  132
  5  ω    -44.00  31.00   0.50    0.30    --  -38.50  19.00-120.00  150
  6  ω    -50.00  24.00   0.50    0.30    --  -38.50  57.00 120.00  148
  7  ω     38.00 112.00   0.50    0.30    --   49.31  57.00 -30.00  148
  8  ω     38.00 112.00   0.50    0.30    --   49.31  57.00  30.00  148
  9  ω     90.00 165.00   0.50    1.11    --  102.63  61.00 -30.00  150
 10  ω     90.00 165.00   0.50    1.11    --  102.63  61.00 -60.00  150
 11  ω     95.00 171.00   0.50    1.11    --  102.63  15.00-150.00  152
 12  ω     38.00 112.00   0.50    1.11    --  102.63-125.00  30.00  148
 13  ω     99.00 171.00   0.50    1.11    --  102.63  30.00 -60.00  144
 14  ω     40.00 116.00   0.50    1.11    --  102.63 -61.00  90.00  152
 15  ω     99.00 171.00   0.50    1.11    --  102.63  30.00  60.00  144
 16  ω     98.00 167.00   0.50    1.11    --  102.63  45.00  30.00  138
 17  ω     98.00 167.00   0.50    1.11    --  102.63  45.00 120.00  138
 18  ω     90.00 165.00   0.50    1.11    --  102.63  61.00   0.00  150
 19  ω     38.00 112.00   0.50    1.11    --  102.63-125.00  60.00  148
 20  ω     35.00 106.00   0.50    1.11    --  102.63 -30.00   0.00  142
 21  ω     38.00 112.00   0.50    1.11    --  102.63-125.00-180.00  148
 22  ω     38.00 107.00   0.50    1.11    --  102.63 -45.00 120.00  138
 23  ω     98.00 167.00   0.50    1.11    --  102.63  45.00   0.00  138
 24  ω     98.00 167.00   0.50    1.11    --  102.63  47.00   1.01  138
 25  ω     95.00 171.00   0.50    1.11    --  102.63  15.00 -60.00  152
 26  ω     38.00 107.00   0.50    1.11    --  102.63 -45.00   0.00  138
 27  ω   -102.00 -19.00   0.50    0.30    --  -38.50 -72.00-118.00  166
 28  ω     38.00 112.00   0.50    0.30    --   49.31  57.00 -90.00  148
 29  ω     38.00 112.00   0.50    0.30    --   49.31  57.00-180.00  148
 30  ω     38.00 112.00   0.50    0.30    --   49.31  57.00  60.00  148
 31  ω     38.00 112.00   0.50    0.30    --   49.31  57.00 120.00  148
 32  ω     38.00 112.00   0.50    0.30    --   49.31  57.00-150.00  148
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'SuperNova, Dual, Cu at home/near, Pilatus 200K'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.2523452000
_diffrn_orient_matrix_UB_12      -0.1988902000
_diffrn_orient_matrix_UB_13      -0.0156040000
_diffrn_orient_matrix_UB_21      0.1801767000
_diffrn_orient_matrix_UB_22      0.0753954000
_diffrn_orient_matrix_UB_23      0.0832668000
_diffrn_orient_matrix_UB_31      -0.1870168000
_diffrn_orient_matrix_UB_32      -0.1954637000
_diffrn_orient_matrix_UB_33      0.0479464000
_diffrn_oxdiff_digest_frames     
;
0188be171ad84768efa723952c0e3c353f000717079
;
_diffrn_oxdiff_digest_hkl        
;
01656af49ff726057aaddf0a18f9926ea748c9
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.769
_reflns_Friedel_fraction_full    0.984
_reflns_Friedel_fraction_max     0.949
_reflns_number_gt                1390
_reflns_number_total             1447
_reflns_odcompleteness_completeness 99.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.438
_refine_diff_density_min         -0.707
_refine_diff_density_rms         0.084
_refine_ls_abs_structure_details 
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.05(8)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.168
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     101
_refine_ls_number_reflns         1447
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0586
_refine_ls_R_factor_gt           0.0573
_refine_ls_restrained_S_all      1.168
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1150P)²+0.2464P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1671
_refine_ls_wR_factor_ref         0.1682
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4)
2.b X=CH2 refined with riding coordinates:
 N3(H3A,H3B)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.1205(2) 0.0423(3) 0.57600(5) 0.0635(4) Uani 1 1 d . . . . .
O1 O 0.621(2) 0.6891(16) 0.8530(6) 0.066(2) Uani 1 1 d . . . . .
H1 H 0.564029 0.636916 0.898359 0.098 Uiso 1 1 calc R U . . .
O2 O 0.3035(17) 0.4233(13) 0.9524(5) 0.0517(15) Uani 1 1 d . . . . .
N1 N 0.590(2) 0.5922(16) 0.7130(6) 0.058(2) Uani 1 1 d . . . . .
N2 N 0.1913(17) 0.1934(14) 0.7431(5) 0.0423(15) Uani 1 1 d . . . . .
N3 N 0.011(2) 0.0989(13) 0.9004(5) 0.050(2) Uani 1 1 d . . . . .
H3A H -0.053194 0.061803 0.949243 0.060 Uiso 1 1 calc R U . . .
H3B H -0.050552 0.011952 0.856801 0.060 Uiso 1 1 calc R U . . .
C1 C 0.5021(18) 0.542(2) 0.7903(5) 0.0460(16) Uani 1 1 d . . . . .
C2 C 0.3008(18) 0.3415(15) 0.8055(6) 0.0378(15) Uani 1 1 d . . . . .
C3 C 0.280(2) 0.2483(17) 0.6668(5) 0.0446(18) Uani 1 1 d . . . . .
C4 C 0.474(3) 0.447(2) 0.6514(7) 0.058(2) Uani 1 1 d . . . . .
H4 H 0.524623 0.479359 0.596139 0.070 Uiso 1 1 calc R U . . .
C5 C 0.204(2) 0.2892(17) 0.8922(6) 0.0411(16) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C3 1.904(10) . ?
O1 H1 0.8200 . ?
O1 C1 1.341(13) . ?
O2 C5 1.245(11) . ?
N1 C1 1.330(12) . ?
N1 C4 1.321(16) . ?
N2 C2 1.329(11) . ?
N2 C3 1.321(11) . ?
N3 H3A 0.8600 . ?
N3 H3B 0.8600 . ?
N3 C5 1.318(11) . ?
C1 C2 1.401(12) . ?
C2 C5 1.484(12) . ?
C3 C4 1.374(15) . ?
C4 H4 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 H1 109.5 . . ?
C4 N1 C1 116.7(9) . . ?
C3 N2 C2 116.2(8) . . ?
H3A N3 H3B 120.0 . . ?
C5 N3 H3A 120.0 . . ?
C5 N3 H3B 120.0 . . ?
O1 C1 C2 121.8(8) . . ?
N1 C1 O1 116.8(9) . . ?
N1 C1 C2 121.4(9) . . ?
N2 C2 C1 121.2(8) . . ?
N2 C2 C5 118.2(7) . . ?
C1 C2 C5 120.6(8) . . ?
N2 C3 Br1 117.1(7) . . ?
N2 C3 C4 122.8(9) . . ?
C4 C3 Br1 120.1(7) . . ?
N1 C4 C3 121.6(9) . . ?
N1 C4 H4 119.2 . . ?
C3 C4 H4 119.2 . . ?
O2 C5 N3 123.6(8) . . ?
O2 C5 C2 120.0(8) . . ?
N3 C5 C2 116.4(8) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br1 C3 C4 N1 -179.6(8) . . . . ?
O1 C1 C2 N2 -178.3(10) . . . . ?
O1 C1 C2 C5 1.7(15) . . . . ?
N1 C1 C2 N2 0.2(14) . . . . ?
N1 C1 C2 C5 -179.8(9) . . . . ?
N2 C2 C5 O2 179.7(8) . . . . ?
N2 C2 C5 N3 -0.9(13) . . . . ?
N2 C3 C4 N1 1.6(16) . . . . ?
C1 N1 C4 C3 -2.1(15) . . . . ?
C1 C2 C5 O2 -0.3(14) . . . . ?
C1 C2 C5 N3 179.1(9) . . . . ?
C2 N2 C3 Br1 -179.0(6) . . . . ?
C2 N2 C3 C4 -0.1(13) . . . . ?
C3 N2 C2 C1 -0.8(12) . . . . ?
C3 N2 C2 C5 179.2(8) . . . . ?
C4 N1 C1 O1 179.8(10) . . . . ?
C4 N1 C1 C2 1.2(15) . . . . ?

_olex2_exptl_crystal_mounting_method 'Mounted on the loop'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.849
_oxdiff_exptl_absorpt_empirical_full_min 0.529
#end_


####################################################################### 
# 
# 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_4a
_database_code_depnum_ccdc_archive 'CCDC 2155452'
loop_
_audit_author_name
_audit_author_address
'Priyanka Ghosh'
;NISER, HBNI
India
;
_audit_update_record             
;
2022-02-28 deposited with the CCDC.	2022-09-21 downloaded from the CCDC.
;
_audit_creation_date             2022-02-28
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C7 H7 Br N2 O3'
_chemical_formula_sum            'C7 H7 Br N2 O3'
_chemical_formula_weight         247.06
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C56 H64 Br8 N16 O24 '
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      tetragonal
_space_group_IT_number           86
_space_group_name_H-M_alt        'P 42/n'
_space_group_name_Hall           '-P 4bc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z'
'-y, x+1/2, z+1/2'
'y+1/2, -x, z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'y, -x-1/2, -z-1/2'
'-y-1/2, x, -z-1/2'

_cell_length_a                   18.4161(7)
_cell_length_b                   18.4161(7)
_cell_length_c                   5.5450(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1880.60(16)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3123
_cell_measurement_temperature    298.8(5)
_cell_measurement_theta_max      70.2460
_cell_measurement_theta_min      4.7790
_shelx_estimated_absorpt_T_max   0.475
_shelx_estimated_absorpt_T_min   0.302
_exptl_absorpt_coefficient_mu    5.824
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.46812
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.745
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             976
_exptl_crystal_preparation       'As per the reaction scheme'
_exptl_crystal_recrystallization_method 'Slow evaporation'
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0407
_diffrn_reflns_av_unetI/netI     0.0327
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            7767
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.343
_diffrn_reflns_theta_min         4.803
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      298.8(5)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.9989
_diffrn_measured_fraction_theta_max 0.9842
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -70.00  23.00   0.50    1.60    --  -38.50  92.00 120.00  186
  2  ω     33.00 106.00   0.50    6.00    --  102.63 -92.00   7.00  146
  3  ω    104.00 171.00   0.50    6.00    --  102.63  92.00 120.00  134
  4  ω   -105.00 -35.00   0.50    1.60    --  -38.50 -38.00 -90.00  140
  5  ω     -1.00  82.00   0.50    1.60    --   49.56 -92.00   7.00  166
  6  ω     35.00 106.00   0.50    6.00    --  102.63 -30.00  30.00  142
  7  ω     98.00 167.00   0.50    6.00    --  102.63  45.00 -90.00  138
  8  ω     98.00 167.00   0.50    6.00    --  102.63  45.00  30.00  138
  9  ω     98.00 167.00   0.50    6.00    --  102.63  45.00-120.00  138
 10  ω     38.00  69.00   0.50    1.60    --   49.56  57.00 150.00   62
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'SuperNova, Dual, Cu at home/near, Pilatus 200K'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0322036000
_diffrn_orient_matrix_UB_12      0.0652532000
_diffrn_orient_matrix_UB_13      -0.1369119000
_diffrn_orient_matrix_UB_21      0.0696406000
_diffrn_orient_matrix_UB_22      -0.0438533000
_diffrn_orient_matrix_UB_23      -0.0494418000
_diffrn_orient_matrix_UB_31      -0.0333888000
_diffrn_orient_matrix_UB_32      -0.0286355000
_diffrn_orient_matrix_UB_33      -0.2364775000
_diffrn_oxdiff_digest_frames     
;
01fbe7884a3624b965386b90a9d884716c00034a2a5
;
_diffrn_oxdiff_digest_hkl        
;
01349174fa67c1d03b7b82d250c7ed79b19e1e
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1432
_reflns_number_total             1908
_reflns_odcompleteness_completeness 99.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.467
_refine_diff_density_min         -0.482
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     120
_refine_ls_number_reflns         1908
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0570
_refine_ls_R_factor_gt           0.0416
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0371P)²+1.3940P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0992
_refine_ls_wR_factor_ref         0.1075
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4)
2.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.32357(3) 0.32615(3) -0.03548(9) 0.0917(2) Uani 1 1 d . . . . .
O1 O 0.39820(16) 0.52885(15) 0.7409(6) 0.0903(9) Uani 1 1 d . . . . .
H1 H 0.433740 0.514899 0.816976 0.135 Uiso 1 1 calc R U . . .
O2 O 0.50814(16) 0.44145(15) 0.8329(6) 0.0897(9) Uani 1 1 d . . . . .
O3 O 0.52136(14) 0.34142(13) 0.6125(5) 0.0779(7) Uani 1 1 d . . . . .
N1 N 0.32469(18) 0.49674(18) 0.4365(7) 0.0816(10) Uani 1 1 d . . . . .
N2 N 0.40657(15) 0.37308(14) 0.3428(5) 0.0596(7) Uani 1 1 d . . . . .
C1 C 0.3829(2) 0.48093(19) 0.5664(7) 0.0683(9) Uani 1 1 d . . . . .
C2 C 0.42433(17) 0.41893(17) 0.5228(6) 0.0588(8) Uani 1 1 d . . . . .
C3 C 0.34932(19) 0.39023(19) 0.2181(7) 0.0659(9) Uani 1 1 d . . . . .
C4 C 0.3079(2) 0.4515(2) 0.2625(8) 0.0792(11) Uani 1 1 d . . . . .
H4 H 0.267419 0.460724 0.167123 0.095 Uiso 1 1 calc R U . . .
C5 C 0.48862(19) 0.40161(19) 0.6715(7) 0.0656(9) Uani 1 1 d . . . . .
C6 C 0.5874(2) 0.3231(3) 0.7440(11) 0.1035(16) Uani 1 1 d . . . . .
H6A H 0.575391 0.301563 0.898674 0.124 Uiso 1 1 calc R U . . .
H6B H 0.616215 0.366333 0.772247 0.124 Uiso 1 1 calc R U . . .
C7 C 0.6280(3) 0.2714(3) 0.5965(15) 0.140(3) Uani 1 1 d . . . . .
H7A H 0.634090 0.290769 0.437116 0.210 Uiso 1 1 calc R U . . .
H7B H 0.601779 0.226400 0.587816 0.210 Uiso 1 1 calc R U . . .
H7C H 0.674763 0.263014 0.667736 0.210 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C3 1.896(4) . ?
O1 H1 0.8200 . ?
O1 C1 1.339(4) . ?
O2 C5 1.212(4) . ?
O3 C5 1.304(4) . ?
O3 C6 1.458(5) . ?
N1 C1 1.324(5) . ?
N1 C4 1.312(5) . ?
N2 C2 1.348(4) . ?
N2 C3 1.300(4) . ?
C1 C2 1.394(5) . ?
C2 C5 1.478(5) . ?
C3 C4 1.383(5) . ?
C4 H4 0.9300 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C7 1.460(8) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?

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
C1 O1 H1 109.5 . . ?
C5 O3 C6 117.2(3) . . ?
C4 N1 C1 116.8(3) . . ?
C3 N2 C2 116.0(3) . . ?
O1 C1 C2 123.3(3) . . ?
N1 C1 O1 114.7(3) . . ?
N1 C1 C2 121.9(3) . . ?
N2 C2 C1 120.6(3) . . ?
N2 C2 C5 118.2(3) . . ?
C1 C2 C5 121.2(3) . . ?
N2 C3 Br1 116.5(3) . . ?
N2 C3 C4 123.4(3) . . ?
C4 C3 Br1 120.1(3) . . ?
N1 C4 C3 121.3(4) . . ?
N1 C4 H4 119.4 . . ?
C3 C4 H4 119.4 . . ?
O2 C5 O3 124.3(3) . . ?
O2 C5 C2 121.3(3) . . ?
O3 C5 C2 114.5(3) . . ?
O3 C6 H6A 110.2 . . ?
O3 C6 H6B 110.2 . . ?
O3 C6 C7 107.3(4) . . ?
H6A C6 H6B 108.5 . . ?
C7 C6 H6A 110.2 . . ?
C7 C6 H6B 110.2 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br1 C3 C4 N1 -179.8(3) . . . . ?
O1 C1 C2 N2 -179.3(3) . . . . ?
O1 C1 C2 C5 0.7(6) . . . . ?
N1 C1 C2 N2 0.8(6) . . . . ?
N1 C1 C2 C5 -179.2(3) . . . . ?
N2 C2 C5 O2 178.6(3) . . . . ?
N2 C2 C5 O3 -1.1(5) . . . . ?
N2 C3 C4 N1 0.2(6) . . . . ?
C1 N1 C4 C3 0.0(6) . . . . ?
C1 C2 C5 O2 -1.4(6) . . . . ?
C1 C2 C5 O3 178.9(3) . . . . ?
C2 N2 C3 Br1 -179.9(2) . . . . ?
C2 N2 C3 C4 0.0(5) . . . . ?
C3 N2 C2 C1 -0.5(5) . . . . ?
C3 N2 C2 C5 179.5(3) . . . . ?
C4 N1 C1 O1 179.6(4) . . . . ?
C4 N1 C1 C2 -0.5(6) . . . . ?
C5 O3 C6 C7 -159.5(4) . . . . ?
C6 O3 C5 O2 -2.7(6) . . . . ?
C6 O3 C5 C2 176.9(4) . . . . ?

_olex2_exptl_crystal_mounting_method 'Mounted on the loop'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.609
_oxdiff_exptl_absorpt_empirical_full_min 0.624
####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 2048893'
loop_
_audit_author_name
_audit_author_address
'Chandra Shekhar Purohit'
;National Institute of Science Education and Research, Bhubaneswar
India
;
_audit_update_record             
;
2020-12-07 deposited with the CCDC.	2022-09-21 downloaded from the CCDC.
;
_audit_creation_date             2020-12-07
_audit_creation_method           
;
Olex2 1.3
(compiled Sep 10 2019 10:52:38 for OlexSys, GUI svn.r5938)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        Ethyl_3-oxo-4-hydropyrazine-2-carboxylate
_chemical_formula_moiety         '2(C7 H8 N2 O3), 2(H O0.5)'
_chemical_formula_sum            'C14 H18 N4 O7'
_chemical_formula_weight         354.32
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C4 H4 N4 O4 '
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_H-M_alt        'P 1 2/c 1'
_space_group_name_Hall           '-P 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'

_cell_length_a                   20.5834(5)
_cell_length_b                   5.22440(10)
_cell_length_c                   15.7133(4)
_cell_angle_alpha                90
_cell_angle_beta                 111.662(3)
_cell_angle_gamma                90
_cell_volume                     1570.41(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8546
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      74.6190
_cell_measurement_theta_min      4.6540
_shelx_estimated_absorpt_T_max   0.819
_shelx_estimated_absorpt_T_min   0.745
_exptl_absorpt_coefficient_mu    1.042
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69610
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.63a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.499
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             744
_exptl_crystal_preparation       'AS PER MENTIONED IN PAPER'
_exptl_crystal_recrystallization_method 'SLOW EVAPORATION'
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0414
_diffrn_reflns_av_unetI/netI     0.0275
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            12472
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.177
_diffrn_reflns_theta_min         4.623
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -70.00  24.00   0.50    2.20    --  -38.50  91.00  97.00  188
  2  ω     -3.00  80.00   0.50    2.20    --   48.56 -91.00 -16.00  166
  3  ω     32.00 106.00   0.50    8.79    --  101.38 -91.00 -16.00  148
  4  ω    104.00 171.00   0.50    8.79    --  101.38  91.00  97.00  134
  5  ω    -14.00  60.00   0.50    2.20    --   48.56 -57.00-180.00  148
  6  ω    -14.00  60.00   0.50    2.20    --   48.56 -57.00  30.00  148
  7  ω    103.00 166.00   0.50    8.79    --  101.38  77.00-180.00  126
  8  ω     32.00 109.00   0.50    8.79    --  101.38-111.00 -30.00  154
  9  ω     37.00 106.00   0.50    8.79    --  101.38 -45.00  60.00  138
 10  ω     33.00 105.00   0.50    8.79    --  101.38 -30.00 -90.00  144
 11  ω    103.00 166.00   0.50    8.79    --  101.38  77.00-120.00  126
 12  ω     39.00 115.00   0.50    8.79    --  101.38 -61.00-180.00  152
 13  ω     37.00 106.00   0.50    8.79    --  101.38 -45.00-180.00  138
 14  ω    103.00 166.00   0.50    8.79    --  101.38  77.00 -30.00  126
 15  ω     37.00 112.00   0.50    2.20    --   48.56  57.00 120.00  150
 16  ω     37.00 112.00   0.50    2.20    --   48.56  57.00-150.00  150
 17  ω     37.00 112.00   0.50    2.20    --   48.56  57.00  60.00  150
 18  ω     37.00 112.00   0.50    2.20    --   48.56  57.00 -30.00  150
 19  ω     98.00 129.00   0.50    8.79    --  101.38  30.00  60.00   62
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'SuperNova, Dual, Cu at home/near, Pilatus 200K'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0562744000
_diffrn_orient_matrix_UB_12      0.1408674000
_diffrn_orient_matrix_UB_13      -0.0251176000
_diffrn_orient_matrix_UB_21      0.0476181000
_diffrn_orient_matrix_UB_22      -0.2372019000
_diffrn_orient_matrix_UB_23      0.0282674000
_diffrn_orient_matrix_UB_31      -0.0324155000
_diffrn_orient_matrix_UB_32      -0.1039194000
_diffrn_orient_matrix_UB_33      -0.0984523000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2876
_reflns_number_total             3121
_reflns_odcompleteness_completeness 99.24
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.367
_refine_diff_density_min         -0.288
_refine_diff_density_rms         0.066
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3121
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0519
_refine_ls_R_factor_gt           0.0491
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0900P)²+0.7766P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1356
_refine_ls_wR_factor_ref         0.1385
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C13(H13A,H13B)
2.b Aromatic/amide H refined with riding coordinates:
 N2(H2), C3(H3), C4(H4), N4(H4A), C10(H10), C11(H11)
2.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C14(H14A,H14B,H14C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.95733(6) 1.3232(2) 0.90337(8) 0.0261(3) Uani 1 1 d . . . . .
O2 O 0.90178(6) 0.8924(2) 0.78692(8) 0.0277(3) Uani 1 1 d . . . . .
O3 O 0.79981(6) 0.7951(2) 0.80260(8) 0.0268(3) Uani 1 1 d . . . . .
N1 N 0.86402(7) 0.8645(3) 0.98482(10) 0.0232(3) Uani 1 1 d . . . . .
N2 N 0.95037(7) 1.2763(3) 1.04356(9) 0.0211(3) Uani 1 1 d . . . . .
H2 H 0.977753 1.410077 1.063665 0.025 Uiso 1 1 calc R U . . .
C1 C 0.88767(8) 0.9829(3) 0.92829(11) 0.0209(3) Uani 1 1 d . . . . .
C2 C 0.93416(8) 1.2033(3) 0.95420(11) 0.0204(3) Uani 1 1 d . . . . .
C3 C 0.92690(8) 1.1555(3) 1.10245(11) 0.0219(3) Uani 1 1 d . . . . .
H3 H 0.940020 1.213029 1.163873 0.026 Uiso 1 1 calc R U . . .
C4 C 0.88386(9) 0.9487(3) 1.07206(11) 0.0238(3) Uani 1 1 d . . . . .
H4 H 0.867474 0.861779 1.113350 0.029 Uiso 1 1 calc R U . . .
C5 C 0.86558(9) 0.8845(3) 0.83181(11) 0.0230(3) Uani 1 1 d . . . . .
C6 C 0.77248(10) 0.6881(3) 0.71015(12) 0.0281(4) Uani 1 1 d . . . . .
H6A H 0.788759 0.792500 0.669327 0.034 Uiso 1 1 calc R U . . .
H6B H 0.720751 0.693095 0.686051 0.034 Uiso 1 1 calc R U . . .
C7 C 0.79672(10) 0.4166(3) 0.71100(13) 0.0326(4) Uani 1 1 d . . . . .
H7A H 0.775841 0.344072 0.649308 0.049 Uiso 1 1 calc R U . . .
H7B H 0.782369 0.315256 0.753547 0.049 Uiso 1 1 calc R U . . .
H7C H 0.847782 0.413318 0.730698 0.049 Uiso 1 1 calc R U . . .
O4 O 0.54190(6) -0.3265(2) 0.44420(8) 0.0248(3) Uani 1 1 d . . . . .
O5 O 0.59209(6) 0.0823(2) 0.37404(8) 0.0266(3) Uani 1 1 d . . . . .
O6 O 0.67502(6) 0.3127(2) 0.48067(8) 0.0232(3) Uani 1 1 d . . . . .
N3 N 0.63203(7) 0.1515(3) 0.61114(10) 0.0221(3) Uani 1 1 d . . . . .
N4 N 0.55242(7) -0.2762(3) 0.59233(9) 0.0206(3) Uani 1 1 d . . . . .
H4A H 0.526769 -0.414053 0.587669 0.025 Uiso 1 1 calc R U . . .
C8 C 0.60824(8) 0.0300(3) 0.53170(10) 0.0198(3) Uani 1 1 d . . . . .
C9 C 0.56574(8) -0.2010(3) 0.51638(10) 0.0199(3) Uani 1 1 d . . . . .
C10 C 0.57603(9) -0.1528(3) 0.67326(11) 0.0220(3) Uani 1 1 d . . . . .
H10 H 0.564870 -0.212367 0.723344 0.026 Uiso 1 1 calc R U . . .
C11 C 0.61658(8) 0.0610(3) 0.68164(11) 0.0227(3) Uani 1 1 d . . . . .
H11 H 0.634256 0.147680 0.738791 0.027 Uiso 1 1 calc R U . . .
C12 C 0.62345(8) 0.1410(3) 0.45329(11) 0.0211(3) Uani 1 1 d . . . . .
C13 C 0.68779(9) 0.4448(3) 0.40695(12) 0.0257(4) Uani 1 1 d . . . . .
H13A H 0.644196 0.525450 0.365035 0.031 Uiso 1 1 calc R U . . .
H13B H 0.704500 0.322530 0.371401 0.031 Uiso 1 1 calc R U . . .
C14 C 0.74253(9) 0.6459(3) 0.45014(13) 0.0277(4) Uani 1 1 d . . . . .
H14A H 0.748670 0.751496 0.402102 0.042 Uiso 1 1 calc R U . . .
H14B H 0.786920 0.562788 0.485924 0.042 Uiso 1 1 calc R U . . .
H14C H 0.727601 0.754265 0.490473 0.042 Uiso 1 1 calc R U . . .
O7 O 1.000000 1.3951(3) 0.750000 0.0290(4) Uani 1 2 d S T P . .
H7 H 0.9860(13) 1.303(5) 0.7821(17) 0.042(7) Uiso 1 1 d . . . . .
O8 O 0.500000 -0.3933(3) 0.250000 0.0279(4) Uani 1 2 d S T P . .
H8 H 0.4837(15) -0.306(6) 0.1981(19) 0.058(8) 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 C2 1.241(2) . ?
O2 C5 1.201(2) . ?
O3 C5 1.343(2) . ?
O3 C6 1.461(2) . ?
N1 C1 1.314(2) . ?
N1 C4 1.351(2) . ?
N2 H2 0.8800 . ?
N2 C2 1.372(2) . ?
N2 C3 1.348(2) . ?
C1 C2 1.456(2) . ?
C1 C5 1.504(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.367(2) . ?
C4 H4 0.9500 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.502(2) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
O4 C9 1.2435(19) . ?
O5 C12 1.212(2) . ?
O6 C12 1.334(2) . ?
O6 C13 1.4533(19) . ?
N3 C8 1.323(2) . ?
N3 C11 1.346(2) . ?
N4 H4A 0.8800 . ?
N4 C9 1.377(2) . ?
N4 C10 1.346(2) . ?
C8 C9 1.458(2) . ?
C8 C12 1.495(2) . ?
C10 H10 0.9500 . ?
C10 C11 1.371(2) . ?
C11 H11 0.9500 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.507(2) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
O7 H7 0.82(2) 2_756 ?
O7 H7 0.82(2) . ?
O8 H8 0.88(3) . ?
O8 H8 0.88(3) 2_655 ?

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
C5 O3 C6 116.26(13) . . ?
C1 N1 C4 118.94(14) . . ?
C2 N2 H2 118.0 . . ?
C3 N2 H2 118.0 . . ?
C3 N2 C2 123.97(14) . . ?
N1 C1 C2 123.53(14) . . ?
N1 C1 C5 118.09(14) . . ?
C2 C1 C5 118.38(14) . . ?
O1 C2 N2 120.82(15) . . ?
O1 C2 C1 126.06(15) . . ?
N2 C2 C1 113.11(14) . . ?
N2 C3 H3 120.6 . . ?
N2 C3 C4 118.72(15) . . ?
C4 C3 H3 120.6 . . ?
N1 C4 C3 121.72(15) . . ?
N1 C4 H4 119.1 . . ?
C3 C4 H4 119.1 . . ?
O2 C5 O3 125.23(15) . . ?
O2 C5 C1 123.93(15) . . ?
O3 C5 C1 110.80(13) . . ?
O3 C6 H6A 109.6 . . ?
O3 C6 H6B 109.6 . . ?
O3 C6 C7 110.34(14) . . ?
H6A C6 H6B 108.1 . . ?
C7 C6 H6A 109.6 . . ?
C7 C6 H6B 109.6 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C12 O6 C13 114.76(13) . . ?
C8 N3 C11 119.38(14) . . ?
C9 N4 H4A 117.8 . . ?
C10 N4 H4A 117.8 . . ?
C10 N4 C9 124.34(14) . . ?
N3 C8 C9 122.94(14) . . ?
N3 C8 C12 118.32(14) . . ?
C9 C8 C12 118.70(14) . . ?
O4 C9 N4 120.15(14) . . ?
O4 C9 C8 126.73(14) . . ?
N4 C9 C8 113.12(14) . . ?
N4 C10 H10 120.8 . . ?
N4 C10 C11 118.39(15) . . ?
C11 C10 H10 120.8 . . ?
N3 C11 C10 121.83(15) . . ?
N3 C11 H11 119.1 . . ?
C10 C11 H11 119.1 . . ?
O5 C12 O6 124.06(15) . . ?
O5 C12 C8 123.69(15) . . ?
O6 C12 C8 112.24(13) . . ?
O6 C13 H13A 110.3 . . ?
O6 C13 H13B 110.3 . . ?
O6 C13 C14 107.30(14) . . ?
H13A C13 H13B 108.5 . . ?
C14 C13 H13A 110.3 . . ?
C14 C13 H13B 110.3 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
H7 O7 H7 108(4) . 2_756 ?
H8 O8 H8 118(4) . 2_655 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 O1 -179.20(15) . . . . ?
N1 C1 C2 N2 -0.5(2) . . . . ?
N1 C1 C5 O2 -147.16(16) . . . . ?
N1 C1 C5 O3 34.7(2) . . . . ?
N2 C3 C4 N1 -0.5(2) . . . . ?
C1 N1 C4 C3 1.0(2) . . . . ?
C2 N2 C3 C4 -0.5(2) . . . . ?
C2 C1 C5 O2 32.7(2) . . . . ?
C2 C1 C5 O3 -145.50(14) . . . . ?
C3 N2 C2 O1 179.78(15) . . . . ?
C3 N2 C2 C1 1.0(2) . . . . ?
C4 N1 C1 C2 -0.5(2) . . . . ?
C4 N1 C1 C5 179.34(14) . . . . ?
C5 O3 C6 C7 81.94(18) . . . . ?
C5 C1 C2 O1 1.0(2) . . . . ?
C5 C1 C2 N2 179.69(13) . . . . ?
C6 O3 C5 O2 3.2(2) . . . . ?
C6 O3 C5 C1 -178.67(13) . . . . ?
N3 C8 C9 O4 -179.51(15) . . . . ?
N3 C8 C9 N4 0.8(2) . . . . ?
N3 C8 C12 O5 -162.70(15) . . . . ?
N3 C8 C12 O6 16.8(2) . . . . ?
N4 C10 C11 N3 1.2(2) . . . . ?
C8 N3 C11 C10 -0.8(2) . . . . ?
C9 N4 C10 C11 -0.6(2) . . . . ?
C9 C8 C12 O5 15.0(2) . . . . ?
C9 C8 C12 O6 -165.50(13) . . . . ?
C10 N4 C9 O4 179.93(14) . . . . ?
C10 N4 C9 C8 -0.4(2) . . . . ?
C11 N3 C8 C9 -0.3(2) . . . . ?
C11 N3 C8 C12 177.31(13) . . . . ?
C12 O6 C13 C14 174.90(13) . . . . ?
C12 C8 C9 O4 2.9(2) . . . . ?
C12 C8 C9 N4 -176.76(13) . . . . ?
C13 O6 C12 O5 5.0(2) . . . . ?
C13 O6 C12 C8 -174.49(12) . . . . ?

_olex2_exptl_crystal_mounting_method 'MOUNTED ON LOOP'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.697
_oxdiff_exptl_absorpt_empirical_full_min 0.502
####################################################################### 
# 
# 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_2a
_database_code_depnum_ccdc_archive 'CCDC 2048894'
loop_
_audit_author_name
_audit_author_address
'Chandra Shekhar Purohit'
;National Institute of Science Education and Research, Bhubaneswar
India
;
_audit_update_record             
;
2020-12-07 deposited with the CCDC.	2022-09-21 downloaded from the CCDC.
;
_audit_creation_date             2020-12-07
_audit_creation_method           
;
Olex2 1.3
(compiled Sep 10 2019 10:52:38 for OlexSys, GUI svn.r5938)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
Methyl-6-fluoro-3-hydroxypyrazine-2-carboxylate
_chemical_formula_moiety         '2(C6 H5 F N2 O3)'
_chemical_formula_sum            'C12 H10 F2 N4 O6'
_chemical_formula_weight         344.24
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C22 H14 F8 N10 O8 '
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   4.1240(2)
_cell_length_b                   12.7162(6)
_cell_length_c                   14.3351(9)
_cell_angle_alpha                67.238(5)
_cell_angle_beta                 82.602(5)
_cell_angle_gamma                81.791(4)
_cell_volume                     683.88(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4324
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      77.2610
_cell_measurement_theta_min      3.9580
_shelx_estimated_absorpt_T_max   0.877
_shelx_estimated_absorpt_T_min   0.553
_exptl_absorpt_coefficient_mu    1.344
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83504
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.63a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.672
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             352
_exptl_crystal_preparation       'AS MENTIONED IN PAPER'
_exptl_crystal_recrystallization_method 'SLOW EVAPORATION'
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0323
_diffrn_reflns_av_unetI/netI     0.0363
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.944
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            6244
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.944
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.412
_diffrn_reflns_theta_min         3.789
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.944
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -50.00  20.00   0.50    0.50    --  -38.50  79.00  29.00  140
  2  ω     -5.00  52.00   0.50    0.50    --   48.56 -79.00 -94.00  114
  3  ω    129.00 156.00   0.50    2.00    --  106.21  79.00  29.00   54
  4  ω     87.00 129.00   0.50    2.00    --  106.21 -79.00 -94.00   84
  5  ω    -66.00 -36.00   0.50    0.50    --  -38.50 -37.00 -60.00   60
  6  ω   -105.00 -79.00   0.50    0.50    --  -38.50 -37.00 -60.00   52
  7  ω    -84.00 -18.00   0.50    0.50    --  -38.50 125.00 150.00  132
  8  ω     81.00 112.00   0.50    0.50    --   48.56  57.00 120.00   62
  9  ω    -13.00  51.00   0.50    0.50    --   48.56 -19.00 -30.00  128
 10  ω     59.00 103.00   0.50    0.50    --   48.56  37.00 -60.00   88
 11  ω     47.00  75.00   0.50    0.50    --   48.56  57.00 120.00   56
 12  ω    109.00 169.00   0.50    2.00    --  106.21  45.00   0.00  120
 13  ω    118.00 170.00   0.50    2.00    --  106.21  77.00  90.00  104
 14  ω     39.00  67.00   0.50    2.00    --  106.21 -94.00-180.00   56
 15  ω     44.00  75.00   0.50    2.00    --  106.21 -61.00-180.00   62
 16  ω     50.00  87.00   0.50    2.00    --  106.21 -94.00  30.00   74
 17  ω    103.00 174.00   0.50    2.00    --  106.21  30.00  60.00  142
 18  ω     53.00  95.00   0.50    2.00    --  106.21 -94.00 120.00   84
 19  ω     42.00 109.00   0.50    2.00    --  106.21 -45.00 -30.00  134
 20  ω     80.00 108.00   0.50    2.00    --  106.21-111.00 -30.00   56
 21  ω     38.00  75.00   0.50    2.00    --  106.21-111.00 -30.00   74
 22  ω     77.00 109.00   0.50    2.00    --  106.21-111.00-150.00   64
 23  ω     47.00  80.00   0.50    2.00    --  106.21 -15.00  30.00   66
 24  ω     84.00 113.00   0.50    2.00    --  106.21 -15.00  30.00   58
 25  ω     38.00  74.00   0.50    2.00    --  106.21-111.00-150.00   72
 26  ω     81.00 106.00   0.50    2.00    --  106.21 -94.00-180.00   50
 27  ω    104.00 134.00   0.50    2.00    --  106.21 111.00   0.00   60
 28  ω    139.00 164.00   0.50    2.00    --  106.21 111.00   0.00   50
 29  ω     55.00 100.00   0.50    2.00    --  106.21 -94.00  60.00   90
 30  ω    106.00 169.00   0.50    2.00    --  106.21  61.00 -30.00  126
 31  ω    131.00 171.00   0.50    2.00    --  106.21  77.00 120.00   80
 32  ω     54.00 106.00   0.50    2.00    --  106.21 -94.00 -90.00  104
 33  ω     42.00 107.00   0.50    2.00    --  106.21 -30.00  30.00  130
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'SuperNova, Dual, Cu at home/near, Pilatus 200K'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0326846000
_diffrn_orient_matrix_UB_12      0.0489254000
_diffrn_orient_matrix_UB_13      0.0841041000
_diffrn_orient_matrix_UB_21      0.2884128000
_diffrn_orient_matrix_UB_22      0.0717806000
_diffrn_orient_matrix_UB_23      -0.0540013000
_diffrn_orient_matrix_UB_31      -0.2431616000
_diffrn_orient_matrix_UB_32      0.0994761000
_diffrn_orient_matrix_UB_33      -0.0606782000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2393
_reflns_number_total             2744
_reflns_odcompleteness_completeness 99.84
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT n/a (Sheldrick, 2015)'
_refine_diff_density_max         0.452
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.079
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         2744
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0565
_refine_ls_R_factor_gt           0.0519
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1044P)²+0.0850P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1421
_refine_ls_wR_factor_ref         0.1465
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C9(H9)
2.b Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C12(H12A,H12B,H12C)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1), O4(H4)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 1.2595(2) 0.66505(8) -0.12635(7) 0.0273(3) Uani 1 1 d . . . . .
O1 O 0.2832(3) 0.99469(9) -0.15683(8) 0.0225(3) Uani 1 1 d . . . . .
H1 H 0.201227 0.992574 -0.100972 0.034 Uiso 1 1 calc R U . . .
O2 O 0.2266(3) 0.91155(10) 0.04396(8) 0.0247(3) Uani 1 1 d . . . . .
O3 O 0.5522(3) 0.75443(9) 0.12823(8) 0.0216(3) Uani 1 1 d . . . . .
N1 N 0.8705(3) 0.74832(11) -0.04485(10) 0.0203(3) Uani 1 1 d . . . . .
N2 N 0.6764(3) 0.90619(12) -0.23226(10) 0.0227(3) Uani 1 1 d . . . . .
C1 C 0.6240(3) 0.83170(12) -0.05042(11) 0.0191(3) Uani 1 1 d . . . . .
C2 C 0.5283(4) 0.91091(13) -0.14504(12) 0.0202(3) Uani 1 1 d . . . . .
C3 C 0.9194(4) 0.82397(14) -0.22594(12) 0.0236(3) Uani 1 1 d . . . . .
H3 H 1.029834 0.817711 -0.284651 0.028 Uiso 1 1 calc R U . . .
C4 C 1.0088(4) 0.74691(13) -0.13103(12) 0.0221(3) Uani 1 1 d . . . . .
C5 C 0.4486(4) 0.83691(13) 0.04533(11) 0.0196(3) Uani 1 1 d . . . . .
C6 C 0.3717(4) 0.75478(13) 0.22290(11) 0.0235(3) Uani 1 1 d . . . . .
H6A H 0.143749 0.748192 0.221157 0.035 Uiso 1 1 calc R U . . .
H6B H 0.392981 0.825140 0.230593 0.035 Uiso 1 1 calc R U . . .
H6C H 0.459917 0.691247 0.279069 0.035 Uiso 1 1 calc R U . . .
F2 F 0.2834(2) 0.90882(8) -0.47633(7) 0.0289(3) Uani 1 1 d . . . . .
O4 O 1.2422(3) 0.59865(11) -0.51678(9) 0.0286(3) Uani 1 1 d . . . . .
H4 H 1.268145 0.545401 -0.462238 0.043 Uiso 1 1 calc R U . . .
O5 O 1.1534(3) 0.49115(10) -0.32127(9) 0.0299(3) Uani 1 1 d . . . . .
O6 O 0.7849(3) 0.57068(10) -0.23155(8) 0.0245(3) Uani 1 1 d . . . . .
N3 N 0.5989(3) 0.74484(11) -0.40003(10) 0.0223(3) Uani 1 1 d . . . . .
N4 N 0.9300(3) 0.76617(12) -0.58824(10) 0.0261(3) Uani 1 1 d . . . . .
C7 C 0.8411(4) 0.66529(13) -0.40883(12) 0.0208(3) Uani 1 1 d . . . . .
C8 C 1.0034(4) 0.67586(14) -0.50408(12) 0.0226(3) Uani 1 1 d . . . . .
C9 C 0.6935(4) 0.84425(14) -0.57899(12) 0.0259(3) Uani 1 1 d . . . . .
H9 H 0.635083 0.908321 -0.635711 0.031 Uiso 1 1 calc R U . . .
C10 C 0.5316(4) 0.83030(14) -0.48374(12) 0.0235(3) Uani 1 1 d . . . . .
C11 C 0.9416(4) 0.56659(14) -0.31660(12) 0.0226(3) Uani 1 1 d . . . . .
C12 C 0.8752(4) 0.47497(14) -0.13955(12) 0.0272(4) Uani 1 1 d . . . . .
H12A H 0.806196 0.406082 -0.139737 0.041 Uiso 1 1 calc R U . . .
H12B H 0.769790 0.489558 -0.081403 0.041 Uiso 1 1 calc R U . . .
H12C H 1.109318 0.466078 -0.136776 0.041 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C4 1.3466(17) . ?
O1 H1 0.8200 . ?
O1 C2 1.3351(19) . ?
O2 C5 1.2172(19) . ?
O3 C5 1.3165(19) . ?
O3 C6 1.4626(17) . ?
N1 C1 1.3459(19) . ?
N1 C4 1.298(2) . ?
N2 C2 1.338(2) . ?
N2 C3 1.325(2) . ?
C1 C2 1.406(2) . ?
C1 C5 1.487(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.393(2) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
F2 C10 1.3485(18) . ?
O4 H4 0.8200 . ?
O4 C8 1.3353(19) . ?
O5 C11 1.218(2) . ?
O6 C11 1.3203(19) . ?
O6 C12 1.4540(19) . ?
N3 C7 1.347(2) . ?
N3 C10 1.299(2) . ?
N4 C8 1.337(2) . ?
N4 C9 1.321(2) . ?
C7 C8 1.407(2) . ?
C7 C11 1.484(2) . ?
C9 H9 0.9300 . ?
C9 C10 1.398(2) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 H1 109.5 . . ?
C5 O3 C6 115.00(12) . . ?
C4 N1 C1 115.86(13) . . ?
C3 N2 C2 117.22(14) . . ?
N1 C1 C2 120.67(14) . . ?
N1 C1 C5 118.84(13) . . ?
C2 C1 C5 120.47(13) . . ?
O1 C2 N2 114.13(13) . . ?
O1 C2 C1 124.23(14) . . ?
N2 C2 C1 121.62(14) . . ?
N2 C3 H3 120.1 . . ?
N2 C3 C4 119.78(14) . . ?
C4 C3 H3 120.1 . . ?
F1 C4 C3 118.80(14) . . ?
N1 C4 F1 116.35(14) . . ?
N1 C4 C3 124.85(15) . . ?
O2 C5 O3 124.68(14) . . ?
O2 C5 C1 121.09(13) . . ?
O3 C5 C1 114.22(13) . . ?
O3 C6 H6A 109.5 . . ?
O3 C6 H6B 109.5 . . ?
O3 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C8 O4 H4 109.5 . . ?
C11 O6 C12 115.29(12) . . ?
C10 N3 C7 115.85(14) . . ?
C9 N4 C8 117.44(14) . . ?
N3 C7 C8 120.74(15) . . ?
N3 C7 C11 119.51(13) . . ?
C8 C7 C11 119.74(14) . . ?
O4 C8 N4 115.57(14) . . ?
O4 C8 C7 122.93(15) . . ?
N4 C8 C7 121.49(15) . . ?
N4 C9 H9 120.1 . . ?
N4 C9 C10 119.83(15) . . ?
C10 C9 H9 120.1 . . ?
F2 C10 C9 118.99(14) . . ?
N3 C10 F2 116.39(14) . . ?
N3 C10 C9 124.61(15) . . ?
O5 C11 O6 124.56(15) . . ?
O5 C11 C7 121.74(14) . . ?
O6 C11 C7 113.69(13) . . ?
O6 C12 H12A 109.5 . . ?
O6 C12 H12B 109.5 . . ?
O6 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 O1 178.85(13) . . . . ?
N1 C1 C2 N2 0.2(2) . . . . ?
N1 C1 C5 O2 179.20(13) . . . . ?
N1 C1 C5 O3 -1.7(2) . . . . ?
N2 C3 C4 F1 -179.05(13) . . . . ?
N2 C3 C4 N1 0.0(2) . . . . ?
C1 N1 C4 F1 178.89(12) . . . . ?
C1 N1 C4 C3 -0.2(2) . . . . ?
C2 N2 C3 C4 0.3(2) . . . . ?
C2 C1 C5 O2 -2.3(2) . . . . ?
C2 C1 C5 O3 176.80(12) . . . . ?
C3 N2 C2 O1 -179.15(12) . . . . ?
C3 N2 C2 C1 -0.4(2) . . . . ?
C4 N1 C1 C2 0.1(2) . . . . ?
C4 N1 C1 C5 178.57(12) . . . . ?
C5 C1 C2 O1 0.4(2) . . . . ?
C5 C1 C2 N2 -178.22(13) . . . . ?
C6 O3 C5 O2 2.0(2) . . . . ?
C6 O3 C5 C1 -177.07(11) . . . . ?
N3 C7 C8 O4 -179.24(13) . . . . ?
N3 C7 C8 N4 1.9(2) . . . . ?
N3 C7 C11 O5 178.07(14) . . . . ?
N3 C7 C11 O6 -3.0(2) . . . . ?
N4 C9 C10 F2 -177.73(13) . . . . ?
N4 C9 C10 N3 1.1(3) . . . . ?
C7 N3 C10 F2 178.20(12) . . . . ?
C7 N3 C10 C9 -0.7(2) . . . . ?
C8 N4 C9 C10 0.0(2) . . . . ?
C8 C7 C11 O5 -3.1(2) . . . . ?
C8 C7 C11 O6 175.83(13) . . . . ?
C9 N4 C8 O4 179.62(14) . . . . ?
C9 N4 C8 C7 -1.4(2) . . . . ?
C10 N3 C7 C8 -0.8(2) . . . . ?
C10 N3 C7 C11 178.06(13) . . . . ?
C11 C7 C8 O4 1.9(2) . . . . ?
C11 C7 C8 N4 -176.97(14) . . . . ?
C12 O6 C11 O5 -1.5(2) . . . . ?
C12 O6 C11 C7 179.59(13) . . . . ?

_olex2_exptl_crystal_mounting_method 'MOUNTED ON LOOP'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.508
_oxdiff_exptl_absorpt_empirical_full_min 0.681
