# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2023

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

data_exp_1179_2nh-nh2
_database_code_depnum_ccdc_archive 'CCDC 2194801'
loop_
_audit_author_name
_audit_author_address
Savita
;BITS
India
;
_audit_update_record             
;
2022-11-30 deposited with the CCDC.	2023-02-17 downloaded from the CCDC.
;
_audit_creation_date             2022-08-01
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/4
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H6 N4 O2'
_chemical_formula_sum            'C9 H6 N4 O2'
_chemical_formula_weight         202.18
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   4.89130(10)
_cell_length_b                   9.7299(2)
_cell_length_c                   17.6911(4)
_cell_angle_alpha                90
_cell_angle_beta                 95.712(2)
_cell_angle_gamma                90
_cell_volume                     837.77(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2589
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      79.2050
_cell_measurement_theta_min      5.2260
_shelx_estimated_absorpt_T_max   0.906
_shelx_estimated_absorpt_T_min   0.824
_exptl_absorpt_coefficient_mu    1.009
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70159
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.20a (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'metallic brownish brown'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   brownish
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.603
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_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     0.0339
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            4265
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.541
_diffrn_reflns_theta_min         5.025
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -28.00  52.00   0.50    1.26    --    0.00  77.00 -90.00  160
  2  ω    -19.00   6.00   0.50    1.26    --    0.00 -37.00 -60.00   50
  3  ω    -86.00 -32.00   0.50    1.26    --    0.00 -37.00 -60.00  108
  4  ω     92.00 165.00   0.50    5.05    --  107.20  30.00  90.00  146
  5  ω     39.00  73.00   0.50    5.05    --  107.20 -82.00 -30.00   68
  6  ω     65.00 132.00   0.50    5.05    --  107.20 -82.00-120.00  134
  7  ω     18.00 125.00   0.50    5.05    --  107.20 -82.00  30.00  214
  8  ω     18.00  90.00   0.50    5.05    --  107.20 -15.00 -90.00  144
  9  ω     99.00 130.00   0.50    5.05    --  107.20 -15.00 -90.00   62
 10  ω     85.00 124.00   0.50    5.05    --  107.20 -61.00  30.00   78
 11  ω     23.00  85.00   0.50    5.05    --  107.20 -45.00 150.00  124
 12  ω     94.00 119.00   0.50    5.05    --  107.20 -82.00 -30.00   50
 13  ω     90.00 131.00   0.50    5.05    --  107.20  30.00 150.00   82
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro: Kappa dual offset/far'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1766469000
_diffrn_orient_matrix_UB_12      -0.1124407000
_diffrn_orient_matrix_UB_13      0.0422601000
_diffrn_orient_matrix_UB_21      -0.1739619000
_diffrn_orient_matrix_UB_22      -0.1114600000
_diffrn_orient_matrix_UB_23      -0.0439074000
_diffrn_orient_matrix_UB_31      0.1967447000
_diffrn_orient_matrix_UB_32      0.0024379000
_diffrn_orient_matrix_UB_33      -0.0628093000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1588
_reflns_number_total             1751
_reflns_odcompleteness_completeness 99.14
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_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 1.171.39.20a (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.208
_refine_diff_density_min         -0.339
_refine_diff_density_rms         0.071
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     141
_refine_ls_number_reflns         1751
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0445
_refine_ls_R_factor_gt           0.0416
_refine_ls_restrained_S_all      1.100
_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)+(0.0620P)²+0.1910P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1115
_refine_ls_wR_factor_ref         0.1148
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1C(H1C), C2C(H2C), C3C(H3C), C4C(H4C)
2.b Idealised tetrahedral OH refined as rotating group:
 N3N(H3NA)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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
O1O O 0.1630(2) 0.22936(10) 0.72204(6) 0.0308(3) Uani 1 1 d . . . . .
O2O O 0.7234(2) 0.59275(11) 0.56829(6) 0.0300(3) Uani 1 1 d . . . . .
N1N N 0.5868(2) 0.50491(11) 0.60303(6) 0.0221(3) Uani 1 1 d . . . . .
N2N N 0.2956(3) 0.80359(12) 0.66395(7) 0.0314(3) Uani 1 1 d . . . . .
N3N N 0.0651(2) 0.48572(12) 0.73757(7) 0.0250(3) Uani 1 1 d . . . . .
H3NA H 0.055145 0.569689 0.740156 0.038 Uiso 1 1 calc GR . . . .
H3NB H -0.003(4) 0.4143(19) 0.7592(10) 0.030(4) Uiso 1 1 d . . . . .
N4N N 0.2982(2) 0.31544(11) 0.68276(6) 0.0220(3) Uani 1 1 d . . . . .
C1C C 0.5169(3) 0.12799(14) 0.62338(8) 0.0267(3) Uani 1 1 d . . . . .
H1C H 0.418255 0.064743 0.649231 0.032 Uiso 1 1 calc R . . . .
C2C C 0.7002(3) 0.08415(15) 0.57472(8) 0.0318(3) Uani 1 1 d . . . . .
H2C H 0.726817 -0.009549 0.568085 0.038 Uiso 1 1 calc R . . . .
C3C C 0.8483(3) 0.17855(16) 0.53477(8) 0.0325(3) Uani 1 1 d . . . . .
H3C H 0.970741 0.146587 0.501802 0.039 Uiso 1 1 calc R . . . .
C4C C 0.8148(3) 0.31740(15) 0.54375(8) 0.0275(3) Uani 1 1 d . . . . .
H4C H 0.913910 0.379563 0.517294 0.033 Uiso 1 1 calc R . . . .
C5C C 0.3988(3) 0.54628(13) 0.64961(7) 0.0214(3) Uani 1 1 d . . . . .
C6C C 0.3526(3) 0.69067(14) 0.65618(7) 0.0236(3) Uani 1 1 d . . . . .
C7C C 0.2513(3) 0.45133(13) 0.69109(7) 0.0208(3) Uani 1 1 d . . . . .
C8C C 0.4803(2) 0.26968(13) 0.63365(7) 0.0217(3) Uani 1 1 d . . . . .
C9C C 0.6286(3) 0.36416(13) 0.59351(7) 0.0223(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1O N4N 1.3088(14) . ?
O2O N1N 1.2793(14) . ?
N1N C5C 1.3558(16) . ?
N1N C9C 1.3973(17) . ?
N2N C6C 1.1451(18) . ?
N3N H3NA 0.8200 . ?
N3N H3NB 0.875(19) . ?
N3N C7C 1.3294(16) . ?
N4N C7C 1.3525(16) . ?
N4N C8C 1.3784(17) . ?
C1C H1C 0.9300 . ?
C1C C2C 1.371(2) . ?
C1C C8C 1.4044(18) . ?
C2C H2C 0.9300 . ?
C2C C3C 1.403(2) . ?
C3C H3C 0.9300 . ?
C3C C4C 1.372(2) . ?
C4C H4C 0.9300 . ?
C4C C9C 1.4041(18) . ?
C5C C6C 1.4295(18) . ?
C5C C7C 1.4203(18) . ?
C8C C9C 1.4064(18) . ?

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
O2O N1N C5C 120.80(11) . . ?
O2O N1N C9C 120.48(11) . . ?
C5C N1N C9C 118.71(11) . . ?
H3NA N3N H3NB 137.7 . . ?
C7C N3N H3NA 109.5 . . ?
C7C N3N H3NB 112.6(12) . . ?
O1O N4N C7C 117.88(11) . . ?
O1O N4N C8C 121.34(11) . . ?
C7C N4N C8C 120.77(11) . . ?
C2C C1C H1C 120.4 . . ?
C2C C1C C8C 119.11(13) . . ?
C8C C1C H1C 120.4 . . ?
C1C C2C H2C 119.5 . . ?
C1C C2C C3C 121.00(13) . . ?
C3C C2C H2C 119.5 . . ?
C2C C3C H3C 119.6 . . ?
C4C C3C C2C 120.83(13) . . ?
C4C C3C H3C 119.6 . . ?
C3C C4C H4C 120.5 . . ?
C3C C4C C9C 118.95(13) . . ?
C9C C4C H4C 120.5 . . ?
N1N C5C C6C 117.61(12) . . ?
N1N C5C C7C 122.07(12) . . ?
C7C C5C C6C 120.32(12) . . ?
N2N C6C C5C 174.27(14) . . ?
N3N C7C N4N 116.58(12) . . ?
N3N C7C C5C 124.77(12) . . ?
N4N C7C C5C 118.64(11) . . ?
N4N C8C C1C 119.83(12) . . ?
N4N C8C C9C 120.34(12) . . ?
C1C C8C C9C 119.83(12) . . ?
N1N C9C C4C 120.32(12) . . ?
N1N C9C C8C 119.40(11) . . ?
C4C C9C C8C 120.28(13) . . ?

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
O1O N4N C7C N3N -1.60(17) . . . . ?
O1O N4N C7C C5C 179.23(11) . . . . ?
O1O N4N C8C C1C 1.95(18) . . . . ?
O1O N4N C8C C9C -178.33(11) . . . . ?
O2O N1N C5C C6C 2.16(17) . . . . ?
O2O N1N C5C C7C -177.63(11) . . . . ?
O2O N1N C9C C4C -2.06(18) . . . . ?
O2O N1N C9C C8C 178.59(10) . . . . ?
N1N C5C C7C N3N 179.94(12) . . . . ?
N1N C5C C7C N4N -0.96(19) . . . . ?
N4N C8C C9C N1N -0.92(18) . . . . ?
N4N C8C C9C C4C 179.73(11) . . . . ?
C1C C2C C3C C4C 0.4(2) . . . . ?
C1C C8C C9C N1N 178.80(10) . . . . ?
C1C C8C C9C C4C -0.55(19) . . . . ?
C2C C1C C8C N4N -179.55(12) . . . . ?
C2C C1C C8C C9C 0.73(19) . . . . ?
C2C C3C C4C C9C -0.2(2) . . . . ?
C3C C4C C9C N1N -179.04(12) . . . . ?
C3C C4C C9C C8C 0.3(2) . . . . ?
C5C N1N C9C C4C 177.84(11) . . . . ?
C5C N1N C9C C8C -1.51(18) . . . . ?
C6C C5C C7C N3N 0.1(2) . . . . ?
C6C C5C C7C N4N 179.25(10) . . . . ?
C7C N4N C8C C1C -177.23(11) . . . . ?
C7C N4N C8C C9C 2.48(18) . . . . ?
C8C N4N C7C N3N 177.62(11) . . . . ?
C8C N4N C7C C5C -1.56(18) . . . . ?
C8C C1C C2C C3C -0.7(2) . . . . ?
C9C N1N C5C C6C -177.74(11) . . . . ?
C9C N1N C5C C7C 2.47(18) . . . . ?

_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 1.418
_oxdiff_exptl_absorpt_empirical_full_min 0.710
