# Supplementary Information (SI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2026

####################################################################### 
# 
# 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 2475635'
loop_
_audit_author_name
_audit_author_address
'Pablo Sanz Miguel'
;Universidad de Zaragoza
Spain
;
_audit_update_record             
;
2025-07-24 deposited with the CCDC.	2025-12-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H13 N4 O, N O3'
_chemical_formula_sum            'C7 H13 N5 O4'
_chemical_formula_weight         231.22

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

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.6071(4)
_cell_length_b                   7.9107(5)
_cell_length_c                   10.3623(6)
_cell_angle_alpha                110.660(3)
_cell_angle_beta                 97.406(3)
_cell_angle_gamma                90.598(3)
_cell_volume                     501.63(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9454
_cell_measurement_theta_min      2.76
_cell_measurement_theta_max      30.21

_exptl_crystal_description       prisms
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.531
_exptl_crystal_F_000             244
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.250
_exptl_absorpt_coefficient_mu    0.126
_shelx_estimated_absorpt_T_min   0.957
_shelx_estimated_absorpt_T_max   0.969
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.922
_exptl_absorpt_correction_T_max  0.969
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11707
_diffrn_reflns_av_unetI/netI     0.0144
_diffrn_reflns_av_R_equivalents  0.0174
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.122
_diffrn_reflns_theta_max         30.210
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.931
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.931
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.931
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2780
_reflns_number_gt                2437
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0617P)²+0.1052P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2780
_refine_ls_number_parameters     197
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0425
_refine_ls_R_factor_gt           0.0375
_refine_ls_wR_factor_ref         0.1074
_refine_ls_wR_factor_gt          0.1031
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.061
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N10 N 0.25176(14) 0.73388(12) 0.37621(8) 0.0233(2) Uani 1 1 d . . . . .
O11 O 0.22314(13) 0.62221(11) 0.25432(8) 0.0303(2) Uani 1 1 d . . . . .
O12 O 0.11497(14) 0.82929(13) 0.42949(8) 0.0382(2) Uani 1 1 d . . . . .
O13 O 0.42504(15) 0.75167(15) 0.44717(9) 0.0496(3) Uani 1 1 d . . . . .
N1 N 0.59604(13) 0.37333(12) 0.17504(9) 0.0238(2) Uani 1 1 d . . . . .
H1 H 0.479(3) 0.417(2) 0.1690(18) 0.044(4) Uiso 1 1 d . . . . .
C1 C 0.73230(17) 0.44822(18) 0.30666(12) 0.0341(3) Uani 1 1 d . . . . .
H11 H 0.859(3) 0.484(2) 0.2880(16) 0.037(4) Uiso 1 1 d . . . . .
H12 H 0.674(3) 0.547(3) 0.365(2) 0.054(5) Uiso 1 1 d . . . . .
H13 H 0.749(3) 0.353(2) 0.3511(19) 0.053(5) Uiso 1 1 d . . . . .
N3 N 0.76125(14) -0.05862(13) -0.19562(9) 0.0257(2) Uani 1 1 d . . . . .
H3 H 0.854(3) -0.029(2) -0.1220(18) 0.039(4) Uiso 1 1 d . . . . .
C3 C 0.79628(16) -0.19652(16) -0.32567(11) 0.0291(2) Uani 1 1 d . . . . .
H31 H 0.691(2) -0.294(2) -0.3550(16) 0.035(4) Uiso 1 1 d . . . . .
H32 H 0.796(2) -0.147(2) -0.4000(17) 0.039(4) Uiso 1 1 d . . . . .
H33 H 0.922(3) -0.232(3) -0.312(2) 0.062(5) Uiso 1 1 d . . . . .
C4 C 0.58881(15) 0.03053(13) -0.18219(10) 0.0202(2) Uani 1 1 d . . . . .
C5 C 0.52789(14) 0.16489(12) -0.06714(9) 0.01827(19) Uani 1 1 d . . . . .
O6 O 0.82207(10) 0.16796(11) 0.08211(8) 0.02742(19) Uani 1 1 d . . . . .
C6 C 0.65485(14) 0.23603(13) 0.06860(10) 0.0198(2) Uani 1 1 d . . . . .
N7 N 0.33323(14) 0.20834(11) -0.11447(8) 0.02167(19) Uani 1 1 d . . . . .
C7 C 0.19653(17) 0.33705(14) -0.03470(10) 0.0247(2) Uani 1 1 d . . . . .
H71 H 0.163(2) 0.3021(18) 0.0391(14) 0.025(3) Uiso 1 1 d . . . . .
H72 H 0.267(2) 0.459(2) 0.0042(15) 0.031(3) Uiso 1 1 d . . . . .
H73 H 0.078(3) 0.331(2) -0.0965(17) 0.038(4) Uiso 1 1 d . . . . .
C8 C 0.28182(18) 0.10708(15) -0.24707(10) 0.0285(2) Uani 1 1 d . . . . .
H8 H 0.163(2) 0.111(2) -0.3016(16) 0.034(4) Uiso 1 1 d . . . . .
N9 N 0.43284(15) -0.00179(12) -0.29098(9) 0.0261(2) Uani 1 1 d . . . . .
H9 H 0.426(3) -0.081(2) -0.3801(19) 0.054(5) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N10 O12 1.2410(12) . ?
N10 O11 1.2486(11) . ?
N10 O13 1.2561(13) . ?
N1 C6 1.3495(12) . ?
N1 C1 1.4573(13) . ?
N1 H1 0.852(18) . ?
C1 H11 0.944(16) . ?
C1 H12 0.93(2) . ?
C1 H13 1.014(19) . ?
N3 C4 1.3429(13) . ?
N3 C3 1.4518(13) . ?
N3 H3 0.875(17) . ?
C3 H31 0.971(16) . ?
C3 H32 0.977(16) . ?
C3 H33 0.89(2) . ?
C4 N9 1.3747(13) . ?
C4 C5 1.3969(12) . ?
C5 N7 1.4066(12) . ?
C5 C6 1.4581(13) . ?
O6 C6 1.2474(12) . ?
N7 C8 1.3200(13) . ?
N7 C7 1.4675(12) . ?
C7 H71 0.949(14) . ?
C7 H72 0.990(15) . ?
C7 H73 0.936(17) . ?
C8 N9 1.3427(13) . ?
C8 H8 0.914(16) . ?
N9 H9 0.910(19) . ?

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
O12 N10 O11 122.18(9) . . ?
O12 N10 O13 118.73(9) . . ?
O11 N10 O13 119.09(9) . . ?
C6 N1 C1 119.80(9) . . ?
C6 N1 H1 122.0(12) . . ?
C1 N1 H1 118.1(12) . . ?
N1 C1 H11 108.2(9) . . ?
N1 C1 H12 108.7(12) . . ?
H11 C1 H12 110.6(15) . . ?
N1 C1 H13 109.0(10) . . ?
H11 C1 H13 111.2(14) . . ?
H12 C1 H13 109.2(15) . . ?
C4 N3 C3 122.53(9) . . ?
C4 N3 H3 116.9(11) . . ?
C3 N3 H3 120.5(11) . . ?
N3 C3 H31 110.4(9) . . ?
N3 C3 H32 111.6(9) . . ?
H31 C3 H32 108.4(13) . . ?
N3 C3 H33 107.4(13) . . ?
H31 C3 H33 113.2(16) . . ?
H32 C3 H33 105.8(16) . . ?
N3 C4 N9 122.33(9) . . ?
N3 C4 C5 130.70(9) . . ?
N9 C4 C5 106.97(8) . . ?
C4 C5 N7 105.51(8) . . ?
C4 C5 C6 123.03(9) . . ?
N7 C5 C6 131.45(8) . . ?
O6 C6 N1 121.06(9) . . ?
O6 C6 C5 117.60(8) . . ?
N1 C6 C5 121.32(9) . . ?
C8 N7 C5 109.01(8) . . ?
C8 N7 C7 122.65(9) . . ?
C5 N7 C7 128.29(8) . . ?
N7 C7 H71 109.6(8) . . ?
N7 C7 H72 109.0(9) . . ?
H71 C7 H72 109.5(12) . . ?
N7 C7 H73 106.6(10) . . ?
H71 C7 H73 109.6(13) . . ?
H72 C7 H73 112.5(13) . . ?
N7 C8 N9 109.52(9) . . ?
N7 C8 H8 125.6(10) . . ?
N9 C8 H8 124.9(10) . . ?
C8 N9 C4 108.99(8) . . ?
C8 N9 H9 122.6(12) . . ?
C4 N9 H9 128.4(12) . . ?

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
C3 N3 C4 N9 -0.28(16) . . . . ?
C3 N3 C4 C5 179.67(11) . . . . ?
N3 C4 C5 N7 179.69(11) . . . . ?
N9 C4 C5 N7 -0.36(11) . . . . ?
N3 C4 C5 C6 0.31(17) . . . . ?
N9 C4 C5 C6 -179.74(9) . . . . ?
C1 N1 C6 O6 2.17(16) . . . . ?
C1 N1 C6 C5 -176.32(10) . . . . ?
C4 C5 C6 O6 -2.52(15) . . . . ?
N7 C5 C6 O6 178.28(10) . . . . ?
C4 C5 C6 N1 176.02(9) . . . . ?
N7 C5 C6 N1 -3.19(16) . . . . ?
C4 C5 N7 C8 0.33(12) . . . . ?
C6 C5 N7 C8 179.63(11) . . . . ?
C4 C5 N7 C7 177.70(10) . . . . ?
C6 C5 N7 C7 -2.99(17) . . . . ?
C5 N7 C8 N9 -0.16(13) . . . . ?
C7 N7 C8 N9 -177.72(10) . . . . ?
N7 C8 N9 C4 -0.08(14) . . . . ?
N3 C4 N9 C8 -179.77(10) . . . . ?
C5 C4 N9 C8 0.28(12) . . . . ?

_refine_diff_density_max         0.412
_refine_diff_density_min         -0.370
_refine_diff_density_rms         0.045

####################################################################### 
# 
# 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_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2475636'
loop_
_audit_author_name
_audit_author_address
'Pablo Sanz Miguel'
;Universidad de Zaragoza
Spain
;
_audit_update_record             
;
2025-07-24 deposited with the CCDC.	2025-12-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H13 N4 O, Cl'
_chemical_formula_sum            'C7 H13 Cl N4 O'
_chemical_formula_weight         204.66

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.5053(3)
_cell_length_b                   7.8928(4)
_cell_length_c                   9.8692(5)
_cell_angle_alpha                68.6656(14)
_cell_angle_beta                 77.5428(14)
_cell_angle_gamma                87.0433(15)
_cell_volume                     460.70(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9820
_cell_measurement_theta_min      2.88
_cell_measurement_theta_max      28.29

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.475
_exptl_crystal_F_000             216
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.110
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.381
_shelx_estimated_absorpt_T_min   0.959
_shelx_estimated_absorpt_T_max   0.981
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.946
_exptl_absorpt_correction_T_max  0.981
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Mo microsource'
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19802
_diffrn_reflns_av_unetI/netI     0.0263
_diffrn_reflns_av_R_equivalents  0.0231
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.267
_diffrn_reflns_theta_max         28.295
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             2285
_reflns_number_gt                2261
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_cell_refinement       'SAINT V8.40B (Bruker AXS, 2016) in APEX3'
_computing_data_collection       'SAINT V8.40B (Bruker AXS, 2016) in APEX3'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS, 2016) in APEX3'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 2012)'
_computing_publication_material  'XCIF program, PLATON(Spek, 1998)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0226P)²+0.2303P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2285
_refine_ls_number_parameters     170
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0276
_refine_ls_R_factor_gt           0.0274
_refine_ls_wR_factor_ref         0.0693
_refine_ls_wR_factor_gt          0.0691
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_restrained_S_all      1.086
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.40283(14) 0.11335(12) 0.67785(10) 0.01618(18) Uani 1 1 d . . . . .
H1 H 0.529(3) 0.073(2) 0.6697(18) 0.026(4) Uiso 1 1 d . . . . .
C1 C 0.25320(17) 0.02674(15) 0.81761(12) 0.0180(2) Uani 1 1 d . . . . .
H11 H 0.234(3) 0.102(2) 0.8774(19) 0.027(4) Uiso 1 1 d . . . . .
H12 H 0.313(3) -0.082(2) 0.8671(18) 0.025(4) Uiso 1 1 d . . . . .
H13 H 0.121(3) 0.004(2) 0.7973(17) 0.023(4) Uiso 1 1 d . . . . .
N3 N 0.27032(14) 0.57538(12) 0.29468(10) 0.01623(18) Uani 1 1 d . . . . .
H3 H 0.165(3) 0.534(2) 0.3691(19) 0.022(4) Uiso 1 1 d . . . . .
C3 C 0.24070(17) 0.70448(15) 0.15272(12) 0.0174(2) Uani 1 1 d . . . . .
H31 H 0.334(3) 0.803(2) 0.1181(19) 0.026(4) Uiso 1 1 d . . . . .
H32 H 0.098(3) 0.745(2) 0.1678(19) 0.028(4) Uiso 1 1 d . . . . .
H33 H 0.257(2) 0.650(2) 0.0825(18) 0.024(4) Uiso 1 1 d . . . . .
C4 C 0.44628(15) 0.48042(13) 0.30604(11) 0.01360(19) Uani 1 1 d . . . . .
C5 C 0.49661(15) 0.33839(13) 0.42677(11) 0.01262(19) Uani 1 1 d . . . . .
C6 C 0.35025(16) 0.25896(13) 0.56907(11) 0.01367(19) Uani 1 1 d . . . . .
O6 O 0.17312(12) 0.32644(10) 0.58518(8) 0.01661(16) Uani 1 1 d . . . . .
N7 N 0.70308(13) 0.29389(11) 0.37659(9) 0.01326(17) Uani 1 1 d . . . . .
C7 C 0.83371(16) 0.15711(14) 0.46019(12) 0.0165(2) Uani 1 1 d . . . . .
H71 H 0.964(3) 0.162(2) 0.3955(19) 0.027(4) Uiso 1 1 d . . . . .
H72 H 0.766(2) 0.038(2) 0.4949(18) 0.023(4) Uiso 1 1 d . . . . .
H73 H 0.852(2) 0.184(2) 0.5426(17) 0.020(3) Uiso 1 1 d . . . . .
C8 C 0.77187(16) 0.40135(14) 0.23680(11) 0.0152(2) Uani 1 1 d . . . . .
H8 H 0.900(3) 0.397(2) 0.1825(18) 0.023(4) Uiso 1 1 d . . . . .
N9 N 0.61990(14) 0.51560(12) 0.19096(10) 0.01503(18) Uani 1 1 d . . . . .
H9 H 0.635(3) 0.599(3) 0.095(2) 0.041(5) Uiso 1 1 d . . . . .
Cl1 Cl 0.26626(4) 0.22154(3) 0.13714(3) 0.01742(9) 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
N1 C6 1.3456(13) . ?
N1 C1 1.4563(13) . ?
N1 H1 0.861(17) . ?
C1 H11 0.966(17) . ?
C1 H12 0.932(17) . ?
C1 H13 0.965(16) . ?
N3 C4 1.3380(13) . ?
N3 C3 1.4477(13) . ?
N3 H3 0.864(17) . ?
C3 H31 0.928(17) . ?
C3 H32 0.968(17) . ?
C3 H33 0.928(16) . ?
C4 N9 1.3756(13) . ?
C4 C5 1.3936(14) . ?
C5 N7 1.4013(12) . ?
C5 C6 1.4546(13) . ?
C6 O6 1.2474(12) . ?
N7 C8 1.3207(13) . ?
N7 C7 1.4588(13) . ?
C7 H71 0.940(17) . ?
C7 H72 0.967(16) . ?
C7 H73 0.942(15) . ?
C8 N9 1.3414(13) . ?
C8 H8 0.895(17) . ?
N9 H9 0.92(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 N1 C1 121.09(9) . . ?
C6 N1 H1 121.1(11) . . ?
C1 N1 H1 117.6(11) . . ?
N1 C1 H11 110.5(10) . . ?
N1 C1 H12 106.0(10) . . ?
H11 C1 H12 109.2(14) . . ?
N1 C1 H13 109.5(9) . . ?
H11 C1 H13 110.7(14) . . ?
H12 C1 H13 111.0(14) . . ?
C4 N3 C3 121.11(9) . . ?
C4 N3 H3 115.4(11) . . ?
C3 N3 H3 121.2(11) . . ?
N3 C3 H31 111.3(10) . . ?
N3 C3 H32 107.2(10) . . ?
H31 C3 H32 109.5(14) . . ?
N3 C3 H33 111.0(10) . . ?
H31 C3 H33 109.6(14) . . ?
H32 C3 H33 108.1(14) . . ?
N3 C4 N9 122.84(9) . . ?
N3 C4 C5 130.11(9) . . ?
N9 C4 C5 107.04(8) . . ?
C4 C5 N7 105.44(8) . . ?
C4 C5 C6 123.50(9) . . ?
N7 C5 C6 131.03(9) . . ?
O6 C6 N1 121.28(9) . . ?
O6 C6 C5 118.00(9) . . ?
N1 C6 C5 120.69(9) . . ?
C8 N7 C5 109.34(8) . . ?
C8 N7 C7 122.60(9) . . ?
C5 N7 C7 128.02(8) . . ?
N7 C7 H71 107.2(10) . . ?
N7 C7 H72 109.7(9) . . ?
H71 C7 H72 110.8(14) . . ?
N7 C7 H73 109.6(9) . . ?
H71 C7 H73 110.2(13) . . ?
H72 C7 H73 109.2(13) . . ?
N7 C8 N9 109.19(9) . . ?
N7 C8 H8 124.6(10) . . ?
N9 C8 H8 126.2(10) . . ?
C8 N9 C4 108.99(9) . . ?
C8 N9 H9 122.6(12) . . ?
C4 N9 H9 128.4(12) . . ?

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
C3 N3 C4 N9 9.16(15) . . . . ?
C3 N3 C4 C5 -172.63(10) . . . . ?
N3 C4 C5 N7 -178.63(10) . . . . ?
N9 C4 C5 N7 -0.21(11) . . . . ?
N3 C4 C5 C6 3.17(17) . . . . ?
N9 C4 C5 C6 -178.40(9) . . . . ?
C1 N1 C6 O6 1.22(15) . . . . ?
C1 N1 C6 C5 -176.57(9) . . . . ?
C4 C5 C6 O6 -2.75(15) . . . . ?
N7 C5 C6 O6 179.56(9) . . . . ?
C4 C5 C6 N1 175.12(9) . . . . ?
N7 C5 C6 N1 -2.58(16) . . . . ?
C4 C5 N7 C8 0.27(11) . . . . ?
C6 C5 N7 C8 178.28(10) . . . . ?
C4 C5 N7 C7 178.27(9) . . . . ?
C6 C5 N7 C7 -3.72(17) . . . . ?
C5 N7 C8 N9 -0.23(11) . . . . ?
C7 N7 C8 N9 -178.36(9) . . . . ?
N7 C8 N9 C4 0.09(12) . . . . ?
N3 C4 N9 C8 178.65(9) . . . . ?
C5 C4 N9 C8 0.08(11) . . . . ?

_refine_diff_density_max         0.391
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.049

####################################################################### 
# 
# 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_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 2475637'
loop_
_audit_author_name
_audit_author_address
'Pablo Sanz Miguel'
;Universidad de Zaragoza
Spain
;
_audit_update_record             
;
2025-11-14 deposited with the CCDC.	2025-12-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H11 N4 O, N O3'
_chemical_formula_sum            'C8 H11 N5 O4'
_chemical_formula_weight         241.22

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

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

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

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

_cell_length_a                   11.7204(8)
_cell_length_b                   8.8224(6)
_cell_length_c                   10.3810(7)
_cell_angle_alpha                90
_cell_angle_beta                 90.9287(9)
_cell_angle_gamma                90
_cell_volume                     1073.28(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6647
_cell_measurement_theta_min      2.31
_cell_measurement_theta_max      28.78

_exptl_crystal_description       prisms
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.493
_exptl_crystal_F_000             504
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.300
_exptl_absorpt_coefficient_mu    0.122
_shelx_estimated_absorpt_T_min   0.959
_shelx_estimated_absorpt_T_max   0.964
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.880
_exptl_absorpt_correction_T_max  0.964
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13369
_diffrn_reflns_av_unetI/netI     0.0278
_diffrn_reflns_av_R_equivalents  0.0315
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.890
_diffrn_reflns_theta_max         29.046
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.942
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.942
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.942
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2697
_reflns_number_gt                2130
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0393P)²+0.4271P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     'Direct methods'
_atom_sites_solution_secondary   'Fourier Difference Synthesis'
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    refU
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0058(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2697
_refine_ls_number_parameters     188
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0537
_refine_ls_R_factor_gt           0.0382
_refine_ls_wR_factor_ref         0.0959
_refine_ls_wR_factor_gt          0.0858
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.17460(9) 0.27419(12) 0.54062(10) 0.0190(2) Uani 1 1 d . . . . .
C1 C 0.08049(12) 0.18733(16) 0.48109(14) 0.0261(3) Uani 1 1 d . . . . .
H11 H 0.0074 0.2297 0.5082 0.035(4) Uiso 1 1 calc R . . . .
H12 H 0.0858 0.0812 0.5083 0.037(5) Uiso 1 1 calc R . . . .
H13 H 0.0856 0.1933 0.3871 0.034(5) Uiso 1 1 calc R . . . .
C2 C 0.15070(11) 0.39507(14) 0.61192(12) 0.0194(3) Uani 1 1 d . . . . .
H2 H 0.0729 0.4212 0.6232 0.020(4) Uiso 1 1 calc R . . . .
N3 N 0.22949(9) 0.48035(12) 0.66766(10) 0.0189(2) Uani 1 1 d . . . . .
C3 C 0.20027(12) 0.61888(15) 0.73910(13) 0.0240(3) Uani 1 1 d . . . . .
H31 H 0.1172 0.6317 0.7389 0.042(5) Uiso 1 1 calc R . . . .
H32 H 0.2355 0.7067 0.6978 0.049(5) Uiso 1 1 calc R . . . .
H33 H 0.2287 0.6104 0.8281 0.031(4) Uiso 1 1 calc R . . . .
C4 C 0.34218(11) 0.44120(14) 0.64956(12) 0.0183(3) Uani 1 1 d . . . . .
C5 C 0.36960(11) 0.31619(14) 0.57717(12) 0.0179(3) Uani 1 1 d . . . . .
O6 O 0.30156(8) 0.11049(11) 0.44781(9) 0.0264(2) Uani 1 1 d . . . . .
C6 C 0.28735(11) 0.22137(14) 0.51506(12) 0.0192(3) Uani 1 1 d . . . . .
N7 N 0.48693(9) 0.31334(12) 0.57820(10) 0.0190(2) Uani 1 1 d . . . . .
C7 C 0.56098(11) 0.20303(16) 0.51575(13) 0.0236(3) Uani 1 1 d . . . . .
H71 H 0.6397 0.2406 0.5172 0.029(4) Uiso 1 1 calc R . . . .
H72 H 0.5354 0.1883 0.4263 0.031(4) Uiso 1 1 calc R . . . .
H73 H 0.5575 0.1063 0.5619 0.028(4) Uiso 1 1 calc R . . . .
C8 C 0.52079(12) 0.43376(15) 0.64972(12) 0.0218(3) Uani 1 1 d . . . . .
H8 H 0.5987 0.4577 0.6660 0.027(4) Uiso 1 1 calc R . . . .
N9 N 0.43489(9) 0.51592(13) 0.69533(10) 0.0208(2) Uani 1 1 d . . . . .
N10 N -0.15298(10) 0.48915(13) 0.69417(11) 0.0237(3) Uani 1 1 d . . . . .
O11 O -0.15873(11) 0.40260(12) 0.59885(10) 0.0348(3) Uani 1 1 d . . . . .
O12 O -0.2341(5) 0.5712(6) 0.7205(5) 0.0258(13) Uani 0.60(3) 1 d . . P A 1
O13 O -0.0643(7) 0.4854(14) 0.7618(7) 0.0392(14) Uani 0.60(3) 1 d . . P A 1
O14 O -0.2399(10) 0.542(3) 0.744(2) 0.078(3) Uani 0.40(3) 1 d . . P A 2
O15 O -0.0601(10) 0.534(2) 0.7405(18) 0.047(3) Uani 0.40(3) 1 d . . P A 2


_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
N1 C2 1.3304(16) . ?
N1 C6 1.4301(16) . ?
N1 C1 1.4709(17) . ?
C1 H11 0.9800 . ?
C1 H12 0.9800 . ?
C1 H13 0.9800 . ?
C2 N3 1.3178(17) . ?
C2 H2 0.9500 . ?
N3 C4 1.3810(16) . ?
N3 C3 1.4729(16) . ?
C3 H31 0.9800 . ?
C3 H32 0.9800 . ?
C3 H33 0.9800 . ?
C4 N9 1.3506(17) . ?
C4 C5 1.3756(18) . ?
C5 N7 1.3752(16) . ?
C5 C6 1.4230(18) . ?
O6 C6 1.2149(16) . ?
N7 C8 1.3519(17) . ?
N7 C7 1.4625(16) . ?
C7 H71 0.9800 . ?
C7 H72 0.9800 . ?
C7 H73 0.9800 . ?
C8 N9 1.3337(18) . ?
C8 H8 0.9500 . ?
N10 O12 1.229(6) . ?
N10 O14 1.243(11) . ?
N10 O13 1.245(7) . ?
N10 O15 1.246(11) . ?
N10 O11 1.2508(15) . ?

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 N1 C6 124.60(11) . . ?
C2 N1 C1 119.22(11) . . ?
C6 N1 C1 116.17(11) . . ?
N1 C1 H11 109.5 . . ?
N1 C1 H12 109.5 . . ?
H11 C1 H12 109.5 . . ?
N1 C1 H13 109.5 . . ?
H11 C1 H13 109.5 . . ?
H12 C1 H13 109.5 . . ?
N3 C2 N1 123.34(12) . . ?
N3 C2 H2 118.3 . . ?
N1 C2 H2 118.3 . . ?
C2 N3 C4 117.55(11) . . ?
C2 N3 C3 121.86(11) . . ?
C4 N3 C3 120.45(11) . . ?
N3 C3 H31 109.5 . . ?
N3 C3 H32 109.5 . . ?
H31 C3 H32 109.5 . . ?
N3 C3 H33 109.5 . . ?
H31 C3 H33 109.5 . . ?
H32 C3 H33 109.5 . . ?
N9 C4 C5 112.94(11) . . ?
N9 C4 N3 126.57(12) . . ?
C5 C4 N3 120.48(12) . . ?
N7 C5 C4 104.65(11) . . ?
N7 C5 C6 131.52(12) . . ?
C4 C5 C6 123.80(12) . . ?
O6 C6 C5 129.46(12) . . ?
O6 C6 N1 120.31(12) . . ?
C5 C6 N1 110.22(11) . . ?
C8 N7 C5 105.93(11) . . ?
C8 N7 C7 126.54(11) . . ?
C5 N7 C7 127.53(11) . . ?
N7 C7 H71 109.5 . . ?
N7 C7 H72 109.5 . . ?
H71 C7 H72 109.5 . . ?
N7 C7 H73 109.5 . . ?
H71 C7 H73 109.5 . . ?
H72 C7 H73 109.5 . . ?
N9 C8 N7 113.93(12) . . ?
N9 C8 H8 123.0 . . ?
N7 C8 H8 123.0 . . ?
C8 N9 C4 102.56(11) . . ?
O12 N10 O13 122.1(5) . . ?
O14 N10 O15 115.9(8) . . ?
O12 N10 O11 120.2(3) . . ?
O14 N10 O11 121.8(5) . . ?
O13 N10 O11 117.6(4) . . ?
O15 N10 O11 122.2(6) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 N1 C2 N3 -0.09(19) . . . . ?
C1 N1 C2 N3 -179.26(12) . . . . ?
N1 C2 N3 C4 0.39(18) . . . . ?
N1 C2 N3 C3 176.05(11) . . . . ?
C2 N3 C4 N9 178.10(12) . . . . ?
C3 N3 C4 N9 2.37(19) . . . . ?
C2 N3 C4 C5 -0.87(17) . . . . ?
C3 N3 C4 C5 -176.60(11) . . . . ?
N9 C4 C5 N7 0.00(14) . . . . ?
N3 C4 C5 N7 179.10(11) . . . . ?
N9 C4 C5 C6 -178.00(11) . . . . ?
N3 C4 C5 C6 1.11(19) . . . . ?
N7 C5 C6 O6 1.4(2) . . . . ?
C4 C5 C6 O6 178.78(13) . . . . ?
N7 C5 C6 N1 -178.15(12) . . . . ?
C4 C5 C6 N1 -0.74(17) . . . . ?
C2 N1 C6 O6 -179.33(12) . . . . ?
C1 N1 C6 O6 -0.15(18) . . . . ?
C2 N1 C6 C5 0.24(17) . . . . ?
C1 N1 C6 C5 179.42(11) . . . . ?
C4 C5 N7 C8 0.15(13) . . . . ?
C6 C5 N7 C8 177.93(13) . . . . ?
C4 C5 N7 C7 179.88(11) . . . . ?
C6 C5 N7 C7 -2.3(2) . . . . ?
C5 N7 C8 N9 -0.27(14) . . . . ?
C7 N7 C8 N9 180.00(11) . . . . ?
N7 C8 N9 C4 0.26(14) . . . . ?
C5 C4 N9 C8 -0.15(14) . . . . ?
N3 C4 N9 C8 -179.19(12) . . . . ?

_refine_diff_density_max         0.262
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.045

####################################################################### 
# 
# 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_CCDC3
_database_code_depnum_ccdc_archive 'CCDC 2475641'
loop_
_audit_author_name
_audit_author_address
'Pablo Sanz Miguel'
;Universidad de Zaragoza
Spain
;
_audit_update_record             
;
2025-07-24 deposited with the CCDC.	2025-12-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H13 N4 O, Cl, 3(H2 O)'
_chemical_formula_sum            'C9 H19 Cl N4 O4'
_chemical_formula_weight         282.73

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   13.5822(5)
_cell_length_b                   6.6192(2)
_cell_length_c                   16.0458(7)
_cell_angle_alpha                90
_cell_angle_beta                 109.3822(15)
_cell_angle_gamma                90
_cell_volume                     1360.81(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8915
_cell_measurement_theta_min      3.36
_cell_measurement_theta_max      28.29

_exptl_crystal_description       blocks
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.380
_exptl_crystal_F_000             600
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.294
_shelx_estimated_absorpt_T_min   0.952
_shelx_estimated_absorpt_T_max   0.985
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.921
_exptl_absorpt_correction_T_max  0.985
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Mo microsource'
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            38366
_diffrn_reflns_av_unetI/netI     0.0274
_diffrn_reflns_av_R_equivalents  0.0596
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.399
_diffrn_reflns_theta_max         28.324
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3381
_reflns_number_gt                2928
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_cell_refinement       'SAINT V8.40B (Bruker AXS, 2016) in APEX3'
_computing_data_collection       'SAINT V8.40B (Bruker AXS, 2016) in APEX3'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS, 2016) in APEX3'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 2012)'
_computing_publication_material  'XCIF program, PLATON(Spek, 1998)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0693P)²+1.0391P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3381
_refine_ls_number_parameters     167
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0507
_refine_ls_R_factor_gt           0.0432
_refine_ls_wR_factor_ref         0.1301
_refine_ls_wR_factor_gt          0.1225
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.20493(11) 0.7413(2) 0.35475(9) 0.0222(3) Uani 1 1 d . . . . .
C1 C 0.10962(15) 0.7118(3) 0.27784(13) 0.0327(4) Uani 1 1 d . . . . .
H11 H 0.0621 0.8259 0.2733 0.049 Uiso 1 1 calc R U . . .
H12 H 0.0752 0.5862 0.2851 0.049 Uiso 1 1 calc R U . . .
H13 H 0.1283 0.7039 0.2239 0.049 Uiso 1 1 calc R U . . .
C2 C 0.19716(13) 0.7839(2) 0.43447(11) 0.0201(3) Uani 1 1 d . . . . .
C21 C 0.09295(13) 0.8101(3) 0.44421(14) 0.0270(4) Uani 1 1 d . . . . .
H21 H 0.0992 0.7961 0.5066 0.040 Uiso 1 1 calc R U . . .
H22 H 0.0451 0.7069 0.4094 0.040 Uiso 1 1 calc R U . . .
H23 H 0.0657 0.9445 0.4231 0.040 Uiso 1 1 calc R U . . .
N3 N 0.28245(10) 0.80492(19) 0.50516(9) 0.0171(3) Uani 1 1 d . . . . .
C3 C 0.27747(13) 0.8502(3) 0.59382(11) 0.0223(3) Uani 1 1 d . . . . .
H31 H 0.2366 0.7456 0.6107 0.033 Uiso 1 1 calc R U . . .
H32 H 0.2442 0.9820 0.5928 0.033 Uiso 1 1 calc R U . . .
H33 H 0.3483 0.8531 0.6368 0.033 Uiso 1 1 calc R U . . .
C4 C 0.37913(12) 0.7792(2) 0.49557(10) 0.0164(3) Uani 1 1 d . . . . .
C5 C 0.38770(13) 0.7343(2) 0.41495(11) 0.0191(3) Uani 1 1 d . . . . .
C6 C 0.30057(14) 0.7044(2) 0.33734(11) 0.0229(3) Uani 1 1 d . . . . .
O6 O 0.30132(11) 0.6542(2) 0.26485(8) 0.0323(3) Uani 1 1 d . . . . .
N7 N 0.49391(11) 0.7186(2) 0.43121(10) 0.0205(3) Uani 1 1 d . . . . .
C7 C 0.54585(14) 0.6814(3) 0.36651(12) 0.0258(4) Uani 1 1 d . . . . .
H71 H 0.6216 0.6848 0.3959 0.039 Uiso 1 1 calc R U . . .
H72 H 0.5256 0.7859 0.3207 0.039 Uiso 1 1 calc R U . . .
H73 H 0.5253 0.5485 0.3394 0.039 Uiso 1 1 calc R U . . .
C8 C 0.54028(13) 0.7551(2) 0.51808(11) 0.0206(3) Uani 1 1 d . . . . .
H8 H 0.6138 0.7540 0.5465 0.025 Uiso 1 1 calc R U . . .
N9 N 0.47242(11) 0.7930(2) 0.56027(9) 0.0186(3) Uani 1 1 d . . . . .
Cl1 Cl 0.19398(3) 0.31085(6) 0.46773(3) 0.02646(14) Uani 1 1 d . . . . .
O1W O 0.17304(10) 0.3744(2) 0.65093(9) 0.0291(3) Uani 1 1 d . . . . .
H1W H 0.1752 0.3556 0.5986 0.035 Uiso 1 1 d R U . . .
H2W H 0.1252 0.4711 0.6460 0.035 Uiso 1 1 d R U . . .
O2W O 0.36029(11) 0.5212(2) 0.77111(9) 0.0310(3) Uani 1 1 d . . . . .
H3W H 0.3003 0.4819 0.7338 0.037 Uiso 1 1 d R U . . .
H4W H 0.3465 0.6276 0.7990 0.037 Uiso 1 1 d R U . . .
O3W O 0.46196(12) 0.1822(2) 0.85024(11) 0.0404(4) Uani 1 1 d . . . . .
H5W H 0.4360 0.3058 0.8446 0.049 Uiso 1 1 d R U . . .
H6W H 0.5278 0.1912 0.8811 0.049 Uiso 1 1 d 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
N1 C2 1.348(2) . ?
N1 C6 1.437(2) . ?
N1 C1 1.475(2) . ?
C1 H11 0.9800 . ?
C1 H12 0.9800 . ?
C1 H13 0.9800 . ?
C2 N3 1.333(2) . ?
C2 C21 1.485(2) . ?
C21 H21 0.9800 . ?
C21 H22 0.9800 . ?
C21 H23 0.9800 . ?
N3 C4 1.382(2) . ?
N3 C3 1.477(2) . ?
C3 H31 0.9800 . ?
C3 H32 0.9800 . ?
C3 H33 0.9800 . ?
C4 N9 1.349(2) . ?
C4 C5 1.369(2) . ?
C5 N7 1.382(2) . ?
C5 C6 1.419(2) . ?
C6 O6 1.213(2) . ?
N7 C8 1.347(2) . ?
N7 C7 1.457(2) . ?
C7 H71 0.9800 . ?
C7 H72 0.9800 . ?
C7 H73 0.9800 . ?
C8 N9 1.336(2) . ?
C8 H8 0.9500 . ?
O1W H1W 0.8586 . ?
O1W H2W 0.8964 . ?
O2W H3W 0.8750 . ?
O2W H4W 0.8873 . ?
O3W H5W 0.8836 . ?
O3W H6W 0.8687 . ?

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 N1 C6 125.48(14) . . ?
C2 N1 C1 119.89(16) . . ?
C6 N1 C1 114.43(15) . . ?
N1 C1 H11 109.5 . . ?
N1 C1 H12 109.5 . . ?
H11 C1 H12 109.5 . . ?
N1 C1 H13 109.5 . . ?
H11 C1 H13 109.5 . . ?
H12 C1 H13 109.5 . . ?
N3 C2 N1 120.66(15) . . ?
N3 C2 C21 119.21(16) . . ?
N1 C2 C21 120.13(15) . . ?
C2 C21 H21 109.5 . . ?
C2 C21 H22 109.5 . . ?
H21 C21 H22 109.5 . . ?
C2 C21 H23 109.5 . . ?
H21 C21 H23 109.5 . . ?
H22 C21 H23 109.5 . . ?
C2 N3 C4 118.81(14) . . ?
C2 N3 C3 122.43(14) . . ?
C4 N3 C3 118.74(13) . . ?
N3 C3 H31 109.5 . . ?
N3 C3 H32 109.5 . . ?
H31 C3 H32 109.5 . . ?
N3 C3 H33 109.5 . . ?
H31 C3 H33 109.5 . . ?
H32 C3 H33 109.5 . . ?
N9 C4 C5 112.91(15) . . ?
N9 C4 N3 126.19(15) . . ?
C5 C4 N3 120.90(14) . . ?
C4 C5 N7 104.39(14) . . ?
C4 C5 C6 123.49(16) . . ?
N7 C5 C6 132.05(16) . . ?
O6 C6 C5 127.58(17) . . ?
O6 C6 N1 121.92(16) . . ?
C5 C6 N1 110.50(15) . . ?
C8 N7 C5 106.39(14) . . ?
C8 N7 C7 126.65(15) . . ?
C5 N7 C7 126.88(15) . . ?
N7 C7 H71 109.5 . . ?
N7 C7 H72 109.5 . . ?
H71 C7 H72 109.5 . . ?
N7 C7 H73 109.5 . . ?
H71 C7 H73 109.5 . . ?
H72 C7 H73 109.5 . . ?
N9 C8 N7 113.18(15) . . ?
N9 C8 H8 123.4 . . ?
N7 C8 H8 123.4 . . ?
C8 N9 C4 103.12(14) . . ?
H1W O1W H2W 106.1 . . ?
H3W O2W H4W 106.1 . . ?
H5W O3W H6W 107.2 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 N1 C2 N3 3.4(2) . . . . ?
C1 N1 C2 N3 177.96(15) . . . . ?
C6 N1 C2 C21 -177.30(15) . . . . ?
C1 N1 C2 C21 -2.7(2) . . . . ?
N1 C2 N3 C4 -1.0(2) . . . . ?
C21 C2 N3 C4 179.66(14) . . . . ?
N1 C2 N3 C3 -179.58(14) . . . . ?
C21 C2 N3 C3 1.1(2) . . . . ?
C2 N3 C4 N9 -179.24(14) . . . . ?
C3 N3 C4 N9 -0.6(2) . . . . ?
C2 N3 C4 C5 0.4(2) . . . . ?
C3 N3 C4 C5 179.09(14) . . . . ?
N9 C4 C5 N7 0.20(18) . . . . ?
N3 C4 C5 N7 -179.53(13) . . . . ?
N9 C4 C5 C6 177.56(15) . . . . ?
N3 C4 C5 C6 -2.2(2) . . . . ?
C4 C5 C6 O6 -175.85(17) . . . . ?
N7 C5 C6 O6 0.7(3) . . . . ?
C4 C5 C6 N1 3.9(2) . . . . ?
N7 C5 C6 N1 -179.58(16) . . . . ?
C2 N1 C6 O6 175.20(17) . . . . ?
C1 N1 C6 O6 0.3(2) . . . . ?
C2 N1 C6 C5 -4.5(2) . . . . ?
C1 N1 C6 C5 -179.40(14) . . . . ?
C4 C5 N7 C8 -0.22(17) . . . . ?
C6 C5 N7 C8 -177.25(17) . . . . ?
C4 C5 N7 C7 -177.10(15) . . . . ?
C6 C5 N7 C7 5.9(3) . . . . ?
C5 N7 C8 N9 0.18(19) . . . . ?
C7 N7 C8 N9 177.07(15) . . . . ?
N7 C8 N9 C4 -0.06(18) . . . . ?
C5 C4 N9 C8 -0.09(18) . . . . ?
N3 C4 N9 C8 179.62(15) . . . . ?

_refine_diff_density_max         0.512
_refine_diff_density_min         -0.440
_refine_diff_density_rms         0.066

####################################################################### 
# 
# 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_CCDC4
_database_code_depnum_ccdc_archive 'CCDC 2475638'
loop_
_audit_author_name
_audit_author_address
'Pablo Sanz Miguel'
;Universidad de Zaragoza
Spain
;
_audit_update_record             
;
2025-07-24 deposited with the CCDC.	2025-12-19 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT355_1                   
;
PROBLEM: Long   O-H (X0.82,N0.98A)  O1W      - H2W      .       1.13 Ang.
RESPONSE: Long O-H distances due to hydrogen bonding.
;
_vrf_PLAT355_1_2                 
;
PROBLEM: Long   O-H (X0.82,N0.98A)  O1W      - H1W      .       1.11 Ang.
RESPONSE: Long O-H distances due to hydrogen bonding.
;
# Added during the CSD deposition process: Thursday 24 July 2025 12:02 PM
# end Validation Reply Form


_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H11 N4 O, Cl, H2 O'
_chemical_formula_sum            'C8 H13 Cl N4 O2'
_chemical_formula_weight         232.67

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   11.2219(9)
_cell_length_b                   14.8838(13)
_cell_length_c                   6.4028(5)
_cell_angle_alpha                90
_cell_angle_beta                 102.4031(11)
_cell_angle_gamma                90
_cell_volume                     1044.46(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8605
_cell_measurement_theta_min      2.31
_cell_measurement_theta_max      28.23

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.480
_exptl_crystal_F_000             488
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.250
_exptl_absorpt_coefficient_mu    0.353
_shelx_estimated_absorpt_T_min   0.886
_shelx_estimated_absorpt_T_max   0.917
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.869
_exptl_absorpt_correction_T_max  0.916
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18651
_diffrn_reflns_av_unetI/netI     0.0142
_diffrn_reflns_av_R_equivalents  0.0233
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.308
_diffrn_reflns_theta_max         28.327
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2581
_reflns_number_gt                2339
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0465P)²+0.5691P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2581
_refine_ls_number_parameters     188
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0349
_refine_ls_R_factor_gt           0.0311
_refine_ls_wR_factor_ref         0.0868
_refine_ls_wR_factor_gt          0.0839
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.85521(9) 0.36189(7) 0.11474(17) 0.0142(2) Uani 1 1 d . . . . .
C1 C 0.97502(12) 0.33239(10) 0.2396(2) 0.0208(3) Uani 1 1 d . . . . .
H11 H 0.9895(16) 0.3597(12) 0.378(3) 0.024(4) Uiso 1 1 d . . . . .
H12 H 1.0341(18) 0.3488(13) 0.166(3) 0.030(5) Uiso 1 1 d . . . . .
H13 H 0.9774(16) 0.2691(13) 0.254(3) 0.026(4) Uiso 1 1 d . . . . .
C2 C 0.85072(12) 0.40660(8) -0.0670(2) 0.0144(2) Uani 1 1 d . . . . .
H2 H 0.9225(16) 0.4160(11) -0.107(3) 0.017(4) Uiso 1 1 d . . . . .
N3 N 0.74798(9) 0.43370(7) -0.19297(16) 0.0132(2) Uani 1 1 d . . . . .
C3 C 0.74917(12) 0.49103(9) -0.3806(2) 0.0182(3) Uani 1 1 d . . . . .
H31 H 0.7459(17) 0.5526(13) -0.337(3) 0.027(4) Uiso 1 1 d . . . . .
H32 H 0.8230(17) 0.4790(11) -0.426(3) 0.021(4) Uiso 1 1 d . . . . .
H33 H 0.6779(18) 0.4763(13) -0.492(3) 0.029(5) Uiso 1 1 d . . . . .
C4 C 0.64073(11) 0.41578(8) -0.1280(2) 0.0127(2) Uani 1 1 d . . . . .
C5 C 0.64299(11) 0.37233(8) 0.06342(19) 0.0133(2) Uani 1 1 d . . . . .
C6 C 0.75180(12) 0.34068(8) 0.2013(2) 0.0148(2) Uani 1 1 d . . . . .
O6 O 0.76453(9) 0.30098(7) 0.37137(15) 0.0215(2) Uani 1 1 d . . . . .
N7 N 0.52254(9) 0.36490(7) 0.07512(17) 0.0144(2) Uani 1 1 d . . . . .
C7 C 0.47492(13) 0.32839(10) 0.2533(2) 0.0219(3) Uani 1 1 d . . . . .
H71 H 0.395(2) 0.3116(15) 0.196(3) 0.042(6) Uiso 1 1 d . . . . .
H72 H 0.4880(17) 0.3732(13) 0.366(3) 0.029(5) Uiso 1 1 d . . . . .
H73 H 0.521(2) 0.2722(17) 0.309(4) 0.056(7) Uiso 1 1 d . . . . .
C8 C 0.45743(12) 0.40316(8) -0.1054(2) 0.0158(2) Uani 1 1 d . . . . .
H8 H 0.3729(16) 0.4049(11) -0.130(3) 0.018(4) Uiso 1 1 d . . . . .
N9 N 0.52625(9) 0.43552(7) -0.23490(17) 0.0155(2) Uani 1 1 d . . . . .
Cl1 Cl 0.86819(3) 0.59016(2) 0.19019(5) 0.01801(10) Uani 1 1 d . . . . .
O1W O 0.75754(11) 0.78701(8) 0.0273(2) 0.0334(3) Uani 1 1 d . . . . .
H1W H 0.802(3) 0.810(2) -0.103(5) 0.093(10) Uiso 1 1 d . . . . .
H2W H 0.810(3) 0.723(3) 0.075(6) 0.107(11) 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
N1 C2 1.3321(16) . ?
N1 C6 1.4247(16) . ?
N1 C1 1.4757(16) . ?
C1 H11 0.958(18) . ?
C1 H12 0.925(19) . ?
C1 H13 0.947(19) . ?
C2 N3 1.3203(17) . ?
C2 H2 0.907(18) . ?
N3 C4 1.3814(15) . ?
N3 C3 1.4758(16) . ?
C3 H31 0.961(19) . ?
C3 H32 0.951(18) . ?
C3 H33 0.975(19) . ?
C4 N9 1.3519(16) . ?
C4 C5 1.3809(17) . ?
C5 N7 1.3742(16) . ?
C5 C6 1.4245(18) . ?
C6 O6 1.2201(16) . ?
N7 C8 1.3534(16) . ?
N7 C7 1.4646(16) . ?
C7 H71 0.92(2) . ?
C7 H72 0.97(2) . ?
C7 H73 1.01(2) . ?
C8 N9 1.3381(17) . ?
C8 H8 0.928(17) . ?
O1W H1W 1.11(3) . ?
O1W H2W 1.13(4) . ?

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 N1 C6 124.71(11) . . ?
C2 N1 C1 118.75(11) . . ?
C6 N1 C1 116.54(11) . . ?
N1 C1 H11 109.2(11) . . ?
N1 C1 H12 108.3(12) . . ?
H11 C1 H12 111.3(16) . . ?
N1 C1 H13 110.6(11) . . ?
H11 C1 H13 109.7(16) . . ?
H12 C1 H13 107.7(17) . . ?
N3 C2 N1 123.40(12) . . ?
N3 C2 H2 119.5(11) . . ?
N1 C2 H2 117.0(11) . . ?
C2 N3 C4 117.39(11) . . ?
C2 N3 C3 120.96(11) . . ?
C4 N3 C3 121.18(10) . . ?
N3 C3 H31 107.8(11) . . ?
N3 C3 H32 107.4(11) . . ?
H31 C3 H32 111.0(15) . . ?
N3 C3 H33 108.5(11) . . ?
H31 C3 H33 110.5(15) . . ?
H32 C3 H33 111.5(15) . . ?
N9 C4 C5 112.68(11) . . ?
N9 C4 N3 126.87(11) . . ?
C5 C4 N3 120.44(11) . . ?
N7 C5 C4 104.79(11) . . ?
N7 C5 C6 131.44(11) . . ?
C4 C5 C6 123.69(11) . . ?
O6 C6 C5 129.33(12) . . ?
O6 C6 N1 120.36(12) . . ?
C5 C6 N1 110.31(10) . . ?
C8 N7 C5 106.05(10) . . ?
C8 N7 C7 126.96(11) . . ?
C5 N7 C7 126.88(11) . . ?
N7 C7 H71 106.0(13) . . ?
N7 C7 H72 107.6(11) . . ?
H71 C7 H72 117.3(17) . . ?
N7 C7 H73 109.7(14) . . ?
H71 C7 H73 107.1(18) . . ?
H72 C7 H73 108.9(17) . . ?
N9 C8 N7 113.77(11) . . ?
N9 C8 H8 126.1(11) . . ?
N7 C8 H8 120.1(11) . . ?
C8 N9 C4 102.71(10) . . ?
H1W O1W H2W 99(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 N1 C2 N3 -2.64(19) . . . . ?
C1 N1 C2 N3 178.10(11) . . . . ?
N1 C2 N3 C4 1.38(18) . . . . ?
N1 C2 N3 C3 173.60(11) . . . . ?
C2 N3 C4 N9 -178.20(11) . . . . ?
C3 N3 C4 N9 9.60(19) . . . . ?
C2 N3 C4 C5 0.95(17) . . . . ?
C3 N3 C4 C5 -171.25(11) . . . . ?
N9 C4 C5 N7 -0.03(14) . . . . ?
N3 C4 C5 N7 -179.30(10) . . . . ?
N9 C4 C5 C6 177.05(11) . . . . ?
N3 C4 C5 C6 -2.22(19) . . . . ?
N7 C5 C6 O6 -2.9(2) . . . . ?
C4 C5 C6 O6 -179.16(13) . . . . ?
N7 C5 C6 N1 177.30(12) . . . . ?
C4 C5 C6 N1 1.06(17) . . . . ?
C2 N1 C6 O6 -178.50(12) . . . . ?
C1 N1 C6 O6 0.76(17) . . . . ?
C2 N1 C6 C5 1.30(17) . . . . ?
C1 N1 C6 C5 -179.43(11) . . . . ?
C4 C5 N7 C8 0.14(13) . . . . ?
C6 C5 N7 C8 -176.62(13) . . . . ?
C4 C5 N7 C7 -176.19(12) . . . . ?
C6 C5 N7 C7 7.0(2) . . . . ?
C5 N7 C8 N9 -0.21(14) . . . . ?
C7 N7 C8 N9 176.12(12) . . . . ?
N7 C8 N9 C4 0.18(14) . . . . ?
C5 C4 N9 C8 -0.09(14) . . . . ?
N3 C4 N9 C8 179.12(12) . . . . ?

_refine_diff_density_max         0.367
_refine_diff_density_min         -0.427
_refine_diff_density_rms         0.055

####################################################################### 
# 
# 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_CCDC5
_database_code_depnum_ccdc_archive 'CCDC 2475640'
loop_
_audit_author_name
_audit_author_address
'Pablo Sanz Miguel'
;Universidad de Zaragoza
Spain
;
_audit_update_record             
;
2025-11-14 deposited with the CCDC.	2025-12-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H11 N4 O, I'
_chemical_formula_sum            'C8 H11 I N4 O'
_chemical_formula_weight         306.11

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'

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

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

_cell_length_a                   11.3493(7)
_cell_length_b                   11.5417(7)
_cell_length_c                   8.4397(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1105.52(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9753
_cell_measurement_theta_min      2.99
_cell_measurement_theta_max      28.31

_exptl_crystal_description       blocks
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.839
_exptl_crystal_F_000             592
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    2.873
_shelx_estimated_absorpt_T_min   0.534
_shelx_estimated_absorpt_T_max   0.803
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.663
_exptl_absorpt_correction_T_max  0.795
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Mo microsource'
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            52792
_diffrn_reflns_av_unetI/netI     0.0191
_diffrn_reflns_av_R_equivalents  0.0294
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.517
_diffrn_reflns_theta_max         28.318
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             2745
_reflns_number_gt                2742
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.866
_reflns_Friedel_fraction_max     0.994
_reflns_Friedel_fraction_full    0.992

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

_computing_cell_refinement       'SAINT V8.40B (Bruker AXS, 2016) in APEX3'
_computing_data_collection       'SAINT V8.40B (Bruker AXS, 2016) in APEX3'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS, 2016) in APEX3'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 2012)'
_computing_publication_material  'XCIF program, PLATON(Spek, 1998)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0071P)²+0.3566P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     'Direct methods'
_atom_sites_solution_secondary   'Fourier Difference Synthesis'
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0026(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 1263 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.018(4)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2745
_refine_ls_number_parameters     131
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0110
_refine_ls_R_factor_gt           0.0110
_refine_ls_wR_factor_ref         0.0271
_refine_ls_wR_factor_gt          0.0271
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.068
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.69123(14) 0.32708(14) 0.74121(19) 0.0183(3) Uani 1 1 d . . . . .
C1 C 0.76514(19) 0.42203(17) 0.6807(2) 0.0257(4) Uani 1 1 d . . . . .
H11 H 0.7406 0.4952 0.7296 0.039 Uiso 1 1 calc R U . . .
H12 H 0.7562 0.4275 0.5654 0.039 Uiso 1 1 calc R U . . .
H13 H 0.8478 0.4067 0.7068 0.039 Uiso 1 1 calc R U . . .
C2 C 0.59269(18) 0.35388(15) 0.8186(2) 0.0180(3) Uani 1 1 d . . . . .
H2 H 0.5741 0.4333 0.8341 0.022 Uiso 1 1 calc R U . . .
N3 N 0.51972(13) 0.27502(13) 0.87468(18) 0.0173(3) Uani 1 1 d . . . . .
C3 C 0.41477(15) 0.30921(15) 0.9650(5) 0.0262(3) Uani 1 1 d . . . . .
H31 H 0.4053 0.3935 0.9600 0.039 Uiso 1 1 calc R U . . .
H32 H 0.4239 0.2852 1.0758 0.039 Uiso 1 1 calc R U . . .
H33 H 0.3450 0.2717 0.9197 0.039 Uiso 1 1 calc R U . . .
C4 C 0.54509(16) 0.16047(14) 0.8457(2) 0.0176(3) Uani 1 1 d . . . . .
C5 C 0.64449(16) 0.13021(16) 0.7615(2) 0.0179(3) Uani 1 1 d . . . . .
C6 C 0.72729(16) 0.21169(15) 0.7019(2) 0.0198(4) Uani 1 1 d . . . . .
O6 O 0.81728(14) 0.19483(15) 0.6271(2) 0.0288(3) Uani 1 1 d . . . . .
N7 N 0.64252(15) 0.01114(14) 0.7565(2) 0.0206(3) Uani 1 1 d . . . . .
C7 C 0.72638(19) -0.06570(18) 0.6764(3) 0.0273(4) Uani 1 1 d . . . . .
H71 H 0.7163 -0.1450 0.7157 0.041 Uiso 1 1 calc R U . . .
H72 H 0.8069 -0.0395 0.6981 0.041 Uiso 1 1 calc R U . . .
H73 H 0.7119 -0.0639 0.5620 0.041 Uiso 1 1 calc R U . . .
C8 C 0.54411(18) -0.02117(18) 0.8352(3) 0.0249(4) Uani 1 1 d . . . . .
H8 H 0.5213 -0.0997 0.8485 0.030 Uiso 1 1 calc R U . . .
N9 N 0.48207(15) 0.06771(14) 0.8924(2) 0.0237(3) Uani 1 1 d . . . . .
I1 I 0.43781(2) 0.34188(2) 0.46230(3) 0.02108(5) 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
N1 C2 1.331(2) . ?
N1 C6 1.432(2) . ?
N1 C1 1.472(2) . ?
C1 H11 0.9800 . ?
C1 H12 0.9800 . ?
C1 H13 0.9800 . ?
C2 N3 1.318(2) . ?
C2 H2 0.9500 . ?
N3 C4 1.375(2) . ?
N3 C3 1.468(3) . ?
C3 H31 0.9800 . ?
C3 H32 0.9800 . ?
C3 H33 0.9800 . ?
C4 N9 1.346(2) . ?
C4 C5 1.378(3) . ?
C5 N7 1.375(2) . ?
C5 C6 1.422(3) . ?
C6 O6 1.216(3) . ?
N7 C8 1.352(3) . ?
N7 C7 1.466(3) . ?
C7 H71 0.9800 . ?
C7 H72 0.9800 . ?
C7 H73 0.9800 . ?
C8 N9 1.335(3) . ?
C8 H8 0.9500 . ?

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 N1 C6 124.73(16) . . ?
C2 N1 C1 118.43(16) . . ?
C6 N1 C1 116.68(15) . . ?
N1 C1 H11 109.5 . . ?
N1 C1 H12 109.5 . . ?
H11 C1 H12 109.5 . . ?
N1 C1 H13 109.5 . . ?
H11 C1 H13 109.5 . . ?
H12 C1 H13 109.5 . . ?
N3 C2 N1 122.91(17) . . ?
N3 C2 H2 118.5 . . ?
N1 C2 H2 118.5 . . ?
C2 N3 C4 117.93(16) . . ?
C2 N3 C3 120.70(16) . . ?
C4 N3 C3 121.37(15) . . ?
N3 C3 H31 109.5 . . ?
N3 C3 H32 109.5 . . ?
H31 C3 H32 109.5 . . ?
N3 C3 H33 109.5 . . ?
H31 C3 H33 109.5 . . ?
H32 C3 H33 109.5 . . ?
N9 C4 N3 126.97(18) . . ?
N9 C4 C5 112.58(16) . . ?
N3 C4 C5 120.45(17) . . ?
N7 C5 C4 104.82(16) . . ?
N7 C5 C6 131.38(18) . . ?
C4 C5 C6 123.78(17) . . ?
O6 C6 C5 129.27(19) . . ?
O6 C6 N1 120.60(17) . . ?
C5 C6 N1 110.13(17) . . ?
C8 N7 C5 105.90(16) . . ?
C8 N7 C7 126.58(17) . . ?
C5 N7 C7 127.46(17) . . ?
N7 C7 H71 109.5 . . ?
N7 C7 H72 109.5 . . ?
H71 C7 H72 109.5 . . ?
N7 C7 H73 109.5 . . ?
H71 C7 H73 109.5 . . ?
H72 C7 H73 109.5 . . ?
N9 C8 N7 113.67(18) . . ?
N9 C8 H8 123.2 . . ?
N7 C8 H8 123.2 . . ?
C8 N9 C4 103.02(17) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 N1 C2 N3 3.5(3) . . . . ?
C1 N1 C2 N3 178.74(18) . . . . ?
N1 C2 N3 C4 -2.7(3) . . . . ?
N1 C2 N3 C3 177.4(2) . . . . ?
C2 N3 C4 N9 -179.94(19) . . . . ?
C3 N3 C4 N9 0.0(3) . . . . ?
C2 N3 C4 C5 0.5(3) . . . . ?
C3 N3 C4 C5 -179.6(2) . . . . ?
N9 C4 C5 N7 -0.2(2) . . . . ?
N3 C4 C5 N7 179.47(17) . . . . ?
N9 C4 C5 C6 -178.59(17) . . . . ?
N3 C4 C5 C6 1.0(3) . . . . ?
N7 C5 C6 O6 1.9(3) . . . . ?
C4 C5 C6 O6 179.8(2) . . . . ?
N7 C5 C6 N1 -178.42(19) . . . . ?
C4 C5 C6 N1 -0.4(3) . . . . ?
C2 N1 C6 O6 178.02(19) . . . . ?
C1 N1 C6 O6 2.7(3) . . . . ?
C2 N1 C6 C5 -1.7(3) . . . . ?
C1 N1 C6 C5 -177.09(16) . . . . ?
C4 C5 N7 C8 0.4(2) . . . . ?
C6 C5 N7 C8 178.64(19) . . . . ?
C4 C5 N7 C7 177.81(18) . . . . ?
C6 C5 N7 C7 -3.9(3) . . . . ?
C5 N7 C8 N9 -0.5(2) . . . . ?
C7 N7 C8 N9 -177.96(18) . . . . ?
N7 C8 N9 C4 0.4(2) . . . . ?
N3 C4 N9 C8 -179.74(19) . . . . ?
C5 C4 N9 C8 -0.1(2) . . . . ?

_refine_diff_density_max         0.303
_refine_diff_density_min         -0.444
_refine_diff_density_rms         0.050

####################################################################### 
# 
# 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_CCDC6
_database_code_depnum_ccdc_archive 'CCDC 2475639'
loop_
_audit_author_name
_audit_author_address
'Pablo Sanz Miguel'
;Universidad de Zaragoza
Spain
;
_audit_update_record             
;
2025-11-14 deposited with the CCDC.	2025-12-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H11 N4 O, Br, H2 O'
_chemical_formula_sum            'C8 H13 Br N4 O2'
_chemical_formula_weight         277.13

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   11.4500(3)
_cell_length_b                   15.0573(4)
_cell_length_c                   6.4762(2)
_cell_angle_alpha                90
_cell_angle_beta                 103.1158(9)
_cell_angle_gamma                90
_cell_volume                     1087.41(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9959
_cell_measurement_theta_min      4.29
_cell_measurement_theta_max      28.29

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.693
_exptl_crystal_F_000             560
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.540
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    3.768
_shelx_estimated_absorpt_T_min   0.235
_shelx_estimated_absorpt_T_max   0.584
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.313
_exptl_absorpt_correction_T_max  0.547
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Mo microsource'
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            26996
_diffrn_reflns_av_unetI/netI     0.0237
_diffrn_reflns_av_R_equivalents  0.0432
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.273
_diffrn_reflns_theta_max         28.306
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             2689
_reflns_number_gt                2643
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_cell_refinement       'SAINT V8.40B (Bruker AXS, 2016) in APEX3'
_computing_data_collection       'SAINT V8.40B (Bruker AXS, 2016) in APEX3'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS, 2016) in APEX3'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 2012)'
_computing_publication_material  'XCIF program, PLATON(Spek, 1998)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0256P)²+0.5536P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     'Direct methods'
_atom_sites_solution_secondary   'Fourier Difference Synthesis'
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0073(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2689
_refine_ls_number_parameters     148
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0200
_refine_ls_R_factor_gt           0.0198
_refine_ls_wR_factor_ref         0.0530
_refine_ls_wR_factor_gt          0.0529
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_restrained_S_all      1.083
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.15280(9) 0.35879(7) 0.88567(16) 0.01253(19) Uani 1 1 d . . . . .
C1 C 0.03537(12) 0.32923(9) 0.7605(2) 0.0198(3) Uani 1 1 d . . . . .
H11 H -0.0274 0.3465 0.8332 0.030 Uiso 1 1 calc R U . . .
H12 H 0.0357 0.2645 0.7448 0.030 Uiso 1 1 calc R U . . .
H13 H 0.0197 0.3571 0.6201 0.030 Uiso 1 1 calc R U . . .
C2 C 0.15700(11) 0.40305(8) 1.0647(2) 0.0129(2) Uani 1 1 d . . . . .
H2 H 0.0836 0.4155 1.1040 0.016 Uiso 1 1 calc R U . . .
N3 N 0.25791(9) 0.43065(7) 1.19098(16) 0.01184(19) Uani 1 1 d . . . . .
C3 C 0.25576(12) 0.48750(9) 1.3756(2) 0.0173(2) Uani 1 1 d . . . . .
H31 H 0.1827 0.4755 1.4255 0.026 Uiso 1 1 calc R U . . .
H32 H 0.2571 0.5501 1.3344 0.026 Uiso 1 1 calc R U . . .
H33 H 0.3261 0.4747 1.4894 0.026 Uiso 1 1 calc R U . . .
C4 C 0.36291(11) 0.41407(7) 1.1276(2) 0.0117(2) Uani 1 1 d . . . . .
C5 C 0.36126(10) 0.37101(8) 0.93944(18) 0.0120(2) Uani 1 1 d . . . . .
C6 C 0.25428(11) 0.33876(8) 0.80169(19) 0.0133(2) Uani 1 1 d . . . . .
O6 O 0.24265(9) 0.29964(7) 0.63380(15) 0.0202(2) Uani 1 1 d . . . . .
N7 N 0.47911(9) 0.36500(7) 0.92918(17) 0.0138(2) Uani 1 1 d . . . . .
C7 C 0.52717(13) 0.32906(10) 0.7551(2) 0.0210(3) Uani 1 1 d . . . . .
H71 H 0.6126 0.3158 0.8066 0.032 Uiso 1 1 calc R U . . .
H72 H 0.5170 0.3729 0.6404 0.032 Uiso 1 1 calc R U . . .
H73 H 0.4840 0.2745 0.7017 0.032 Uiso 1 1 calc R U . . .
C8 C 0.54297(12) 0.40384(8) 1.1080(2) 0.0157(2) Uani 1 1 d . . . . .
H8 H 0.6279 0.4085 1.1402 0.019 Uiso 1 1 calc R U . . .
N9 N 0.47520(9) 0.43492(8) 1.23474(17) 0.0148(2) Uani 1 1 d . . . . .
Br1 Br 0.12726(2) 0.58809(2) 0.80431(2) 0.01498(6) Uani 1 1 d . . . . .
O1W O 0.24504(10) 0.79162(8) 0.95514(19) 0.0284(2) Uani 1 1 d . . . . .
H1W H 0.203(3) 0.7327(19) 0.918(4) 0.062(8) Uiso 1 1 d . . . . .
H2W H 0.215(3) 0.815(2) 1.083(5) 0.078(9) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C2 1.3286(16) . ?
N1 C6 1.4226(16) . ?
N1 C1 1.4726(15) . ?
C1 H11 0.9800 . ?
C1 H12 0.9800 . ?
C1 H13 0.9800 . ?
C2 N3 1.3221(16) . ?
C2 H2 0.9500 . ?
N3 C4 1.3785(16) . ?
N3 C3 1.4749(16) . ?
C3 H31 0.9800 . ?
C3 H32 0.9800 . ?
C3 H33 0.9800 . ?
C4 N9 1.3521(16) . ?
C4 C5 1.3767(16) . ?
C5 N7 1.3689(15) . ?
C5 C6 1.4270(16) . ?
C6 O6 1.2170(15) . ?
N7 C8 1.3539(17) . ?
N7 C7 1.4659(16) . ?
C7 H71 0.9800 . ?
C7 H72 0.9800 . ?
C7 H73 0.9800 . ?
C8 N9 1.3358(17) . ?
C8 H8 0.9500 . ?
O1W H1W 1.01(3) . ?
O1W H2W 1.03(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C6 124.68(10) . . ?
C2 N1 C1 118.67(11) . . ?
C6 N1 C1 116.64(10) . . ?
N1 C1 H11 109.5 . . ?
N1 C1 H12 109.5 . . ?
H11 C1 H12 109.5 . . ?
N1 C1 H13 109.5 . . ?
H11 C1 H13 109.5 . . ?
H12 C1 H13 109.5 . . ?
N3 C2 N1 123.44(12) . . ?
N3 C2 H2 118.3 . . ?
N1 C2 H2 118.3 . . ?
C2 N3 C4 117.24(11) . . ?
C2 N3 C3 120.72(11) . . ?
C4 N3 C3 121.50(11) . . ?
N3 C3 H31 109.5 . . ?
N3 C3 H32 109.5 . . ?
H31 C3 H32 109.5 . . ?
N3 C3 H33 109.5 . . ?
H31 C3 H33 109.5 . . ?
H32 C3 H33 109.5 . . ?
N9 C4 C5 112.59(11) . . ?
N9 C4 N3 126.66(11) . . ?
C5 C4 N3 120.74(11) . . ?
N7 C5 C4 104.97(10) . . ?
N7 C5 C6 131.52(11) . . ?
C4 C5 C6 123.44(11) . . ?
O6 C6 N1 120.72(11) . . ?
O6 C6 C5 128.88(12) . . ?
N1 C6 C5 110.40(10) . . ?
C8 N7 C5 106.08(10) . . ?
C8 N7 C7 126.38(11) . . ?
C5 N7 C7 127.44(11) . . ?
N7 C7 H71 109.5 . . ?
N7 C7 H72 109.5 . . ?
H71 C7 H72 109.5 . . ?
N7 C7 H73 109.5 . . ?
H71 C7 H73 109.5 . . ?
H72 C7 H73 109.5 . . ?
N9 C8 N7 113.62(12) . . ?
N9 C8 H8 123.2 . . ?
N7 C8 H8 123.2 . . ?
C8 N9 C4 102.74(11) . . ?
H1W O1W H2W 105(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 N1 C2 N3 -2.91(19) . . . . ?
C1 N1 C2 N3 178.36(11) . . . . ?
N1 C2 N3 C4 1.84(18) . . . . ?
N1 C2 N3 C3 173.54(11) . . . . ?
C2 N3 C4 N9 -178.54(11) . . . . ?
C3 N3 C4 N9 9.83(19) . . . . ?
C2 N3 C4 C5 0.43(17) . . . . ?
C3 N3 C4 C5 -171.20(11) . . . . ?
N9 C4 C5 N7 -0.13(14) . . . . ?
N3 C4 C5 N7 -179.24(10) . . . . ?
N9 C4 C5 C6 177.31(11) . . . . ?
N3 C4 C5 C6 -1.79(18) . . . . ?
C2 N1 C6 O6 -178.26(12) . . . . ?
C1 N1 C6 O6 0.49(17) . . . . ?
C2 N1 C6 C5 1.42(16) . . . . ?
C1 N1 C6 C5 -179.83(10) . . . . ?
N7 C5 C6 O6 -2.8(2) . . . . ?
C4 C5 C6 O6 -179.50(12) . . . . ?
N7 C5 C6 N1 177.56(12) . . . . ?
C4 C5 C6 N1 0.86(16) . . . . ?
C4 C5 N7 C8 0.08(13) . . . . ?
C6 C5 N7 C8 -177.07(12) . . . . ?
C4 C5 N7 C7 -176.44(12) . . . . ?
C6 C5 N7 C7 6.4(2) . . . . ?
C5 N7 C8 N9 -0.01(14) . . . . ?
C7 N7 C8 N9 176.56(12) . . . . ?
N7 C8 N9 C4 -0.07(14) . . . . ?
C5 C4 N9 C8 0.12(14) . . . . ?
N3 C4 N9 C8 179.16(11) . . . . ?

_refine_diff_density_max         0.371
_refine_diff_density_min         -0.465
_refine_diff_density_rms         0.065

####################################################################### 
# 
# 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_cmpnd_2Br_H2O_HR
_database_code_depnum_ccdc_archive 'CCDC 2475642'
loop_
_audit_author_name
_audit_author_address
'Pablo Sanz Miguel'
;Universidad de Zaragoza
Spain
;
_audit_update_record             
;
2025-10-06 deposited with the CCDC.	2025-12-19 downloaded from the CCDC.
;

_audit_creation_method           'MoPro rev2700,  2024-03  '
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C8 H11 N4 O, Br, 0.804(H2 O)'
_chemical_formula_sum            'C8 H12.6 Br N4 O1.8'
_chemical_formula_weight         273.579
_chemical_absolute_configuration .

_symmetry_cell_setting           monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016
'Clementi & Roetti 1974. Atomic Data & Nuclear Data Tables. 14, 177'
H H 0.0000 0.0000
'Clementi & Roetti 1974. Atomic Data & Nuclear Data Tables. 14, 177'
N N 0.0061 0.0033
'Clementi & Roetti 1974. Atomic Data & Nuclear Data Tables. 14, 177'
O O 0.0106 0.0060
'Clementi & Roetti 1974. Atomic Data & Nuclear Data Tables. 14, 177'
Br Br -0.2901 2.4595
'Clementi & Roetti 1974. Atomic Data & Nuclear Data Tables. 14, 177'

loop_
_symmetry_equiv_pos_as_xyz
' x , y , z '
' -x , y+1/2 , -z+1/2 '
' -x , -y , -z '
' x , -y-1/2 , z-1/2 '
_cell_length_a                   11.4461(5)
_cell_length_b                   15.0792(7)
_cell_length_c                   6.4594(3)
_cell_angle_alpha                90.
_cell_angle_beta                 103.2320(10)
_cell_angle_gamma                90.
_cell_volume                     1085.28(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9522
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      52.09
_cell_measurement_theta_min      3.26



_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.158
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.110

_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.675
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             552.16

_exptl_absorpt_coefficient_mu    3.773
_exptl_absorpt_correction_T_max  0.7503
_exptl_absorpt_correction_T_min  0.6437
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0722 before and 0.0512 after correction.
The Ratio of minimum to maximum transmission is 0.8579.
The λ/2 correction factor is Not present.
;

_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Photon III'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'Bruker Photon III area detector'
_diffrn_measurement_device       'Bruker Photon III , D8 Venture diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'high brilliance microfocus sealed tube'
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_type              'Diamond  Incoatec Microfocus Source '

_diffrn_reflns_number            276116
_diffrn_reflns_av_R_equivalents  0.0437
_diffrn_reflns_av_sigmaI/netI    0.01623
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.27
_diffrn_reflns_theta_max         51.42
_reflns_number_total             10432
_reflns_number_gt                10426

### _reflns_number_gt  : I/weighted_sigmaI > 2
_reflns_threshold_expression     'I > 2 σ(I)'

_computing_cell_refinement       'SAINT V8.40B (Bruker AXS, 2016)'
_computing_data_collection       'SAINT V8.40B (Bruker AXS, 2016)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS, 2016)'

_computing_structure_solution    'XS  (Sheldrick, 2008)'
_computing_structure_refinement  'MoPro (J. Appl. Cryst. 2005, 38, 38-54)'
_computing_molecular_graphics    MoProViewer
_computing_publication_material  'MoPro (J. Appl. Cryst. 2005, 38, 38-54)'



_refine_special_details          
;
 Refinement of F² against reflections.
 The threshold expression of F² > 2sigma(F²) is
 used for calculating R-factors(gt) and is not
 relevant to the choice of reflections for refinement.
 R-factors based on F² are statistically about twice
 as large as those based on F, and R-factors based on
 ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     ?
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    ?
# refall refxyz hetero heteroxyz constr

_refine_ls_extinction_method     none
_refine_ls_abs_structure_Flack   ?
_refine_ls_abs_structure_Rogers  ?
###  Notice MoPro refines Rogers parameter (Eta f" multiplier)

_refine_ls_number_reflns         10432
_refine_ls_number_parameters     480
_refine_ls_number_restraints     201
# R_factor is R(F)  &  wR_factor is wR2(I)
## Refinement was performed using a cutoff  I/sigmaI >    0.00
## R_factor_gt is computed  for  I/sigmaI > 2
_refine_ls_R_factor_all          0.0143
_refine_ls_R_factor_gt           0.0143
_refine_ls_wR_factor_ref         0.0330
_refine_ls_wR_factor_gt          0.0329
_refine_ls_goodness_of_fit_ref   1.022
# GOF(I) computed assuming all  740 parameters refined:     1.036
_refine_ls_restrained_S_all      0.335
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000

_diffrn_measured_fraction_theta_max 0.862
_diffrn_reflns_theta_full        30.30
_diffrn_measured_fraction_theta_full 0.982
_refine_diff_density_max         0.31
_refine_diff_density_min         -0.48
_refine_diff_density_rms         0.06
###  to get diff_density_max min & rms :
###  run MoPro  : WRIT FOUR   to create FOURier file
### run VMoPro : FOUR  FastFourierTransform
### to get a 3D grid (Xplor format) on whole unit-cell
###  To get max min rms statistics
###  run VMoPro: GRID STAT   or
###  open 3D xplor grid with MoProViewer

loop_
_atom_site_type_symbol
_atom_site_label
_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_calc_flag
_atom_site_refinement_flag_posn
_atom_site_refinement_flag_adp
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br1 0.127850(3) 0.588131(2) 0.805266(6) 0.015911(5) Uani 1 d . . . .
N N1 0.15202(3) 0.35865(2) 0.88452(5) 0.01326(3) Uani 1 d . . . .
N N3 0.25729(3) 0.43073(2) 1.19114(5) 0.01228(3) Uani 1 d . . . .
N N7 0.47899(3) 0.36509(2) 0.92940(6) 0.01435(3) Uani 1 d . . . .
N N9 0.47466(3) 0.43519(2) 1.23540(5) 0.01482(3) Uani 1 d . . . .
O O6 0.24134(5) 0.29984(3) 0.63194(7) 0.02049(4) Uani 1 d . . . .
C C1 0.03470(3) 0.32887(3) 0.75975(6) 0.02045(4) Uani 1 d . . . .
H H11 -0.0349(4) 0.3516(5) 0.8375(11) 0.04141 Uani 1 d D U . .
H H12 0.0339(6) 0.2568(2) 0.7507(12) 0.04323 Uani 1 d D U . .
H H13 0.0194(6) 0.3570(5) 0.6004(6) 0.04294 Uani 1 d D U . .
C C2 0.15633(3) 0.40312(2) 1.06408(5) 0.01318(3) Uani 1 d . . . .
H H2 0.0731(4) 0.4149(5) 1.1109(10) 0.02953 Uani 1 d D U . .
C C3 0.25501(3) 0.48744(3) 1.37509(6) 0.01762(3) Uani 1 d . . . .
H H31 0.1734(4) 0.4729(4) 1.4302(10) 0.04031 Uani 1 d D U . .
H H32 0.2553(6) 0.5568(2) 1.3272(10) 0.03947 Uani 1 d D U . .
H H33 0.3342(4) 0.4730(4) 1.5010(8) 0.04017 Uani 1 d D U . .
C C4 0.36219(3) 0.414240(19) 1.12870(5) 0.01175(3) Uani 1 d . . . .
C C5 0.36080(3) 0.37105(2) 0.93912(5) 0.01236(3) Uani 1 d . . . .
C C6 0.25346(3) 0.33889(2) 0.80125(5) 0.01366(3) Uani 1 d . . . .
C C7 0.52646(4) 0.32921(3) 0.75537(8) 0.02260(5) Uani 1 d . . . .
H H71 0.6228(3) 0.3170(5) 0.8135(11) 0.04495 Uani 1 d D U . .
H H72 0.5123(7) 0.3772(4) 0.6256(8) 0.04289 Uani 1 d D U . .
H H73 0.4804(6) 0.2672(3) 0.7013(11) 0.04360 Uani 1 d D U . .
C C8 0.54280(3) 0.40407(2) 1.10910(6) 0.01584(4) Uani 1 d . . . .
H H8 0.6396(4) 0.4086(5) 1.1443(10) 0.03409 Uani 1 d D U . .
O O1W 0.24671(6) 0.79107(4) 0.95779(11) 0.02352(7) Uani 0.80 d . . . .
H H1W 0.2071(10) 0.7335(4) 0.929(2) 0.0361(4) Uiso 0.80 d D . . .
H H2W 0.2052(10) 0.8179(8) 1.0589(15) 0.0362(4) Uiso 0.80 d D . . .


_geom_special_details            
;
;

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
N1 C6 1.4184(4) . ?
N1 C2 1.3309(4) . ?
N1 C1 1.4694(5) . ?
N3 C4 1.3740(4) . ?
N3 C2 1.3222(4) . ?
N3 C3 1.4690(4) . ?
N7 C8 1.3558(5) . ?
N7 C5 1.3715(4) . ?
N7 C7 1.4599(5) . ?
N9 C4 1.3512(4) . ?
N9 C8 1.3362(5) . ?
O6 C6 1.2217(5) . ?
C1 H12 1.088(3) . ?
C1 H13 1.090(3) . ?
C1 H11 1.090(3) . ?
C2 H2 1.079(5) . ?
C3 H32 1.091(3) . ?
C3 H33 1.093(3) . ?
C3 H31 1.095(3) . ?
C4 C5 1.3838(4) . ?
C5 C6 1.4272(4) . ?
C7 H73 1.091(3) . ?
C7 H72 1.092(3) . ?
C7 H71 1.096(3) . ?
C8 H8 1.081(5) . ?
O1W H1W 0.977(4) . ?
O1W H2W 0.979(4) . ?

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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 N1 C2 124.48(3) . . . ?
C6 N1 C1 116.90(3) . . . ?
C2 N1 C1 118.61(3) . . . ?
C4 N3 C2 117.33(2) . . . ?
C4 N3 C3 121.42(2) . . . ?
C2 N3 C3 120.70(3) . . . ?
C8 N7 C5 106.03(3) . . . ?
C8 N7 C7 126.69(3) . . . ?
C5 N7 C7 127.19(3) . . . ?
C4 N9 C8 103.15(3) . . . ?
N1 C1 H12 109.3(3) . . . ?
N1 C1 H13 109.2(3) . . . ?
N1 C1 H11 108.9(3) . . . ?
H12 C1 H13 109.9(5) . . . ?
H12 C1 H11 109.9(6) . . . ?
H13 C1 H11 109.7(5) . . . ?
N3 C2 N1 123.53(3) . . . ?
N3 C2 H2 118.5(2) . . . ?
N1 C2 H2 117.9(2) . . . ?
N3 C3 H32 109.1(3) . . . ?
N3 C3 H33 108.7(3) . . . ?
N3 C3 H31 108.7(3) . . . ?
H32 C3 H33 110.3(5) . . . ?
H32 C3 H31 110.0(5) . . . ?
H33 C3 H31 110.0(5) . . . ?
N3 C4 N9 127.05(3) . . . ?
N3 C4 C5 120.73(2) . . . ?
N9 C4 C5 112.21(3) . . . ?
N7 C5 C6 131.79(3) . . . ?
N7 C5 C4 105.05(3) . . . ?
C6 C5 C4 123.10(2) . . . ?
O6 C6 N1 120.38(3) . . . ?
O6 C6 C5 128.86(3) . . . ?
N1 C6 C5 110.76(2) . . . ?
N7 C7 H73 109.1(3) . . . ?
N7 C7 H72 109.2(3) . . . ?
N7 C7 H71 108.7(3) . . . ?
H73 C7 H72 110.3(5) . . . ?
H73 C7 H71 109.9(6) . . . ?
H72 C7 H71 109.6(5) . . . ?
N7 C8 N9 113.56(3) . . . ?
N7 C8 H8 122.2(2) . . . ?
N9 C8 H8 124.2(2) . . . ?
H1W O1W H2W 103.(1) . . . ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
N1 C6 C5 N7 . . . . 177.46(5) ?
N1 C6 C5 C4 . . . . 0.86(5) ?
N1 C2 N3 C4 . . . . 1.93(4) ?
N1 C2 N3 C3 . . . . 173.56(4) ?
N3 C4 N9 C8 . . . . 179.22(4) ?
N3 C4 C5 N7 . . . . -179.31(4) ?
N3 C4 C5 C6 . . . . -1.93(4) ?
N3 C2 N1 C6 . . . . -3.15(4) ?
N3 C2 N1 C1 . . . . 178.05(4) ?
N7 C8 N9 C4 . . . . 0.15(4) ?
N7 C5 C6 O6 . . . . -3.08(7) ?
N7 C5 C4 N9 . . . . 0.11(4) ?
N9 C4 N3 C2 . . . . -178.79(5) ?
N9 C4 N3 C3 . . . . 9.64(5) ?
N9 C4 C5 C6 . . . . 177.48(5) ?
N9 C8 N7 C5 . . . . -0.09(4) ?
N9 C8 N7 C7 . . . . 176.45(5) ?
O6 C6 N1 C2 . . . . -177.92(6) ?
O6 C6 N1 C1 . . . . 0.90(6) ?
O6 C6 C5 C4 . . . . -179.68(6) ?
C1 N1 C6 C5 . . . . -179.59(5) ?
C1 N1 C2 H2 . . . . 0.5(6) ?
H11 C1 N1 C6 . . . . -176.9(7) ?
H11 C1 N1 C2 . . . . 2.0(7) ?
H12 C1 N1 C6 . . . . 63.1(7) ?
H12 C1 N1 C2 . . . . -118.1(7) ?
H13 C1 N1 C6 . . . . -57.2(7) ?
H13 C1 N1 C2 . . . . 121.7(7) ?
C2 N3 C4 C5 . . . . 0.53(4) ?
C2 N3 C3 H32 . . . . -91.3(3) ?
C2 N3 C3 H33 . . . . 148.5(4) ?
C2 N3 C3 H31 . . . . 28.7(4) ?
C2 N1 C6 C5 . . . . 1.59(4) ?
H2 C2 N3 C4 . . . . 179.5(7) ?
H2 C2 N3 C3 . . . . -8.9(8) ?
H2 C2 N1 C6 . . . . 179.3(8) ?
C3 N3 C4 C5 . . . . -171.04(5) ?
H31 C3 N3 C4 . . . . -160.0(7) ?
H32 C3 N3 C4 . . . . 80.0(7) ?
H33 C3 N3 C4 . . . . -40.2(7) ?
C4 N9 C8 H8 . . . . -179.6(6) ?
C4 C5 N7 C8 . . . . 0.00(4) ?
C4 C5 N7 C7 . . . . -176.53(5) ?
C5 N7 C8 H8 . . . . 179.6(6) ?
C5 N7 C7 H73 . . . . -44.6(4) ?
C5 N7 C7 H72 . . . . 76.0(3) ?
C5 N7 C7 H71 . . . . -164.4(5) ?
C5 C4 N9 C8 . . . . -0.15(4) ?
C6 C5 N7 C8 . . . . -177.06(4) ?
C6 C5 N7 C7 . . . . 6.42(5) ?
C7 N7 C8 H8 . . . . -3.8(7) ?
H71 C7 N7 C8 . . . . 19.8(8) ?
H72 C7 N7 C8 . . . . -99.8(8) ?
H73 C7 N7 C8 . . . . 139.6(8) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
### Notice sigmas on distances involving HYDROGEN atoms
### is generally not recommended.
### this may cause reading errors in checkcif
O1W H1W Br1 0.977(4) 2.436(5) 3.4019(7) 169.6(3) 1
C7 H73 N7 1.091(3) 2.655(5) 3.5762(6) 141.7(3) 4_565
C2 H2 Br1 1.079(5) 2.481(5) 3.5449(3) 168.8(3) 3_567
C3 H32 O1W 1.091(3) 2.454(4) 3.3870(8) 142.7(2) 4_576
O1W H2W Br1 0.979(4) 2.443(5) 3.4065(6) 168.0(3) 4_576
C7 H71 O1W 1.096(3) 2.579(6) 3.2564(7) 119.1(3) 2_646
C7 H71 O1W 1.096(3) 2.461(6) 3.3558(9) 137.9(3) 3_667

#---------------------------------------------#
#   ANHARMONIC PARAMETERS                     #
#---------------------------------------------#

loop_
_atom_site_anharm_GC_C_label
_atom_site_anharm_GC_C_111
_atom_site_anharm_GC_C_222
_atom_site_anharm_GC_C_333
_atom_site_anharm_GC_C_112
_atom_site_anharm_GC_C_122
_atom_site_anharm_GC_C_113
_atom_site_anharm_GC_C_133
_atom_site_anharm_GC_C_223
_atom_site_anharm_GC_C_233
_atom_site_anharm_GC_C_123
_atom_site_anharm_GC_C_1111
_atom_site_anharm_GC_C_2222
_atom_site_anharm_GC_C_3333
_atom_site_anharm_GC_C_1112
_atom_site_anharm_GC_C_1113
_atom_site_anharm_GC_C_1122
_atom_site_anharm_GC_C_1123
_atom_site_anharm_GC_C_1133
_atom_site_anharm_GC_C_1222
_atom_site_anharm_GC_C_1223
_atom_site_anharm_GC_C_1233
_atom_site_anharm_GC_C_1333
_atom_site_anharm_GC_C_2223
_atom_site_anharm_GC_C_2233
_atom_site_anharm_GC_C_2333
Br1 -0.000018 -0.000003 0.000767 -0.000060 -0.000050 -0.000118 0.000115
-0.000033 0.000341 -0.000156 -0.000013 0.000008 0.000483 0.000018 0.000108
0.000031 0.000093 0.000331 0.000024 0.000085 0.000271 0.000549 0.000029
0.000166 0.000259

#---------------------------------------------#
#   MULTIPOLE PARAMETERS                      #
#---------------------------------------------#

loop_
_atom_rho_multipole_atom_label
_atom_rho_multipole_coeff_Pv
_atom_rho_multipole_coeff_P00
_atom_rho_multipole_coeff_P11
_atom_rho_multipole_coeff_P1-1
_atom_rho_multipole_coeff_P10
_atom_rho_multipole_coeff_P20
_atom_rho_multipole_coeff_P21
_atom_rho_multipole_coeff_P2-1
_atom_rho_multipole_coeff_P22
_atom_rho_multipole_coeff_P2-2
_atom_rho_multipole_coeff_P30
_atom_rho_multipole_coeff_P31
_atom_rho_multipole_coeff_P3-1
_atom_rho_multipole_coeff_P32
_atom_rho_multipole_coeff_P3-2
_atom_rho_multipole_coeff_P33
_atom_rho_multipole_coeff_P3-3
_atom_rho_multipole_coeff_P40
_atom_rho_multipole_coeff_P41
_atom_rho_multipole_coeff_P4-1
_atom_rho_multipole_coeff_P42
_atom_rho_multipole_coeff_P4-2
_atom_rho_multipole_coeff_P43
_atom_rho_multipole_coeff_P4-3
_atom_rho_multipole_coeff_P44
_atom_rho_multipole_coeff_P4-4
_atom_rho_multipole_kappa
_atom_rho_multipole_kappa_prime1
_atom_rho_multipole_radial_slater_n0
_atom_rho_multipole_radial_slater_zeta0
_atom_rho_multipole_radial_slater_n1
_atom_rho_multipole_radial_slater_zeta1
_atom_rho_multipole_radial_slater_n2
_atom_rho_multipole_radial_slater_zeta2
_atom_rho_multipole_radial_slater_n3
_atom_rho_multipole_radial_slater_zeta3
_atom_rho_multipole_radial_slater_n4
_atom_rho_multipole_radial_slater_zeta4
Br1 7.67(7) 0. -0.067(7) 0.039(7) -0.015(8) -0.034(14) 0.050(7) -0.008(13)
0.116(12) 0.075(8) 0.033(7) 0.018(6) 0.029(6) -0.055(6) 0.012(6) -0.040(6)
-0.009(6) 0.047(11) -0.049(8) -0.005(10) -0.137(10) -0.057(8) 0.109(8) 0.074(9)
0.012(8) 0.035(8) 0.970(4) 1.236 4 4.650 4 4.650 4 4.650 4 4.650 4 4.650
N1 5.09(5) 0. 0.006(11) -0.034(11) -0.013(10) -0.020(10) -0.035(9) 0.013(9)
-0.003(10) 0.027(10) -0.007(10) 0.028(9) 0.044(9) 0.005(9) 0.003(9) -0.215(10)
-0.013(10) 0. 0. 0. 0. 0. 0. 0. 0. 0. 0.997(4) 0.950 2 3.839 2 3.839 2 3.839 3
3.839 4 3.839
N3 4.95(6) 0. 0.019(12) 0.061(13) -0.006(11) -0.025(11) -0.004(10) 0.000(10)
0.028(11) 0.049(11) -0.021(10) 0.009(10) 0.004(9) 0.011(10) -0.019(10)
-0.239(11) -0.013(11) 0. 0. 0. 0. 0. 0. 0. 0. 0. 1.005(4) 0.933 2 3.839 2 3.839
2 3.839 3 3.839 4 3.839
N7 5.11(5) 0. 0.083(10) -0.090(10) 0.006(9) -0.042(10) -0.036(9) 0.008(9)
0.013(9) -0.048(10) 0.001(9) -0.003(9) 0.026(9) -0.016(9) -0.032(9) -0.247(9)
0.002(10) 0. 0. 0. 0. 0. 0. 0. 0. 0. 0.999(4) 1.010 2 3.839 2 3.839 2 3.839 3
3.839 4 3.839
N9 5.15(5) 0. -0.120(11) -0.005(12) 0.019(11) -0.114(11) 0.009(10) 0.032(10)
0.094(10) -0.015(11) 0.007(10) -0.031(9) -0.007(9) 0.009(9) 0.005(9) -0.106(10)
-0.012(9) 0. 0. 0. 0. 0. 0. 0. 0. 0. 0.988(4) 1.004 2 3.839 2 3.839 2 3.839 3
3.839 4 3.839
O6 6.23(4) 0. -0.016(10) -0.158(10) 0.088(11) -0.052(12) -0.001(10) -0.005(11)
-0.079(11) -0.017(10) 0.017(9) 0.026(8) -0.030(8) -0.069(8) 0.000(8) -0.004(8)
-0.047(8) 0. 0. 0. 0. 0. 0. 0. 0. 0. 0.979(3) 1.042 2 4.466 2 4.466 2 4.466 3
4.466 4 4.466
C1 4.23(6) 0. 0.016(13) 0.044(14) -0.097(15) -0.150(13) 0.004(12) -0.019(13)
-0.024(13) 0.031(13) 0.254(17) -0.046(15) 0.010(15) 0.003(14) -0.012(14)
0.249(15) -0.094(16) 0. 0. 0. 0. 0. 0. 0. 0. 0. 1.009(5) 0.938 2 3.176 2 3.176
2 3.176 3 3.176 4 3.176
H11 0.869(9) 0. 0. 0. 0.129(6) 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0.
0. 0. 0. 0. 0. 1.174(8) 1.175 2 2.000 1 2.000 2 2.000 3 2.000 4 2.000
H12 0.868(9) 0. 0. 0. 0.129(6) 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0.
0. 0. 0. 0. 0. 1.176(11) 1.189 2 2.000 1 2.000 2 2.000 3 2.000 4 2.000
H13 0.869(9) 0. 0. 0. 0.128(6) 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0.
0. 0. 0. 0. 0. 1.181(11) 1.187 2 2.000 1 2.000 2 2.000 3 2.000 4 2.000
C2 3.97(7) 0. -0.046(15) 0.026(14) -0.030(11) -0.215(12) -0.007(10) -0.002(11)
-0.010(13) 0.026(12) 0.022(13) 0.029(11) -0.046(11) -0.008(12) 0.030(12)
-0.288(15) -0.011(14) 0. 0. 0. 0. 0. 0. 0. 0. 0. 1.014(6) 0.989 2 3.176 2 3.176
2 3.176 3 3.176 4 3.176
H2 0.81(2) 0. 0. 0. 0.141(16) 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0.
0. 0. 0. 0. 0. 1.167(10) 1.162 2 2.000 1 2.000 2 2.000 3 2.000 4 2.000
C3 4.05(6) 0. 0.037(12) 0.025(12) -0.121(12) -0.151(11) 0.022(10) 0.016(10)
-0.003(10) 0.004(10) 0.222(13) 0.028(11) -0.014(11) -0.007(12) 0.010(11)
0.140(12) -0.012(13) 0. 0. 0. 0. 0. 0. 0. 0. 0. 0.996(5) 1.007 2 3.176 2 3.176
2 3.176 3 3.176 4 3.176
H31 0.870(9) 0. 0. 0. 0.127(6) 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0.
0. 0. 0. 0. 0. 1.188(11) 1.183 2 2.000 1 2.000 2 2.000 3 2.000 4 2.000
H32 0.868(9) 0. 0. 0. 0.129(6) 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0.
0. 0. 0. 0. 0. 1.162(11) 1.189 2 2.000 1 2.000 2 2.000 3 2.000 4 2.000
H33 0.868(9) 0. 0. 0. 0.129(6) 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0.
0. 0. 0. 0. 0. 1.164(11) 1.187 2 2.000 1 2.000 2 2.000 3 2.000 4 2.000
C4 3.88(8) 0. -0.093(17) 0.079(15) 0.000(12) -0.143(13) 0.020(12) 0.013(9)
0.022(14) 0.008(12) 0.011(15) -0.015(11) 0.021(12) 0.000(13) -0.032(13)
-0.300(16) 0.006(14) 0. 0. 0. 0. 0. 0. 0. 0. 0. 1.015(7) 0.969 2 3.176 2 3.176
2 3.176 3 3.176 4 3.176
C5 4.06(7) 0. 0.048(13) 0.025(13) 0.018(12) -0.096(12) -0.040(10) -0.020(11)
-0.069(12) -0.041(12) 0.035(12) 0.004(12) -0.046(12) 0.022(12) 0.012(12)
-0.166(14) -0.067(13) 0. 0. 0. 0. 0. 0. 0. 0. 0. 1.006(6) 0.979 2 3.176 2 3.176
2 3.176 3 3.176 4 3.176
C6 3.87(7) 0. -0.067(14) -0.134(14) -0.045(11) -0.228(12) -0.024(10) -0.016(10)
0.041(12) -0.137(12) 0.045(13) 0.051(12) 0.035(12) 0.049(12) -0.005(12)
-0.307(15) -0.026(13) 0. 0. 0. 0. 0. 0. 0. 0. 0. 1.004(6) 0.996 2 3.176 2 3.176
2 3.176 3 3.176 4 3.176
C7 4.19(6) 0. -0.057(12) 0.145(13) -0.090(12) -0.162(12) -0.024(12) 0.032(11)
-0.022(12) 0.021(13) 0.191(14) 0.019(12) -0.074(12) 0.001(12) -0.104(12)
0.180(13) 0.055(14) 0. 0. 0. 0. 0. 0. 0. 0. 0. 0.978(6) 1.047 2 3.176 2 3.176 2
3.176 3 3.176 4 3.176
H71 0.868(9) 0. 0. 0. 0.127(6) 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0.
0. 0. 0. 0. 0. 1.157(11) 1.182 2 2.000 1 2.000 2 2.000 3 2.000 4 2.000
H72 0.869(9) 0. 0. 0. 0.128(6) 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0.
0. 0. 0. 0. 0. 1.160(11) 1.187 2 2.000 1 2.000 2 2.000 3 2.000 4 2.000
H73 0.868(9) 0. 0. 0. 0.129(6) 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0.
0. 0. 0. 0. 0. 1.143(11) 1.188 2 2.000 1 2.000 2 2.000 3 2.000 4 2.000
C8 4.06(7) 0. -0.043(17) 0.115(17) 0.004(11) -0.154(14) 0.025(11) 0.002(12)
0.093(14) 0.074(14) -0.007(15) 0.046(13) -0.040(12) 0.024(14) -0.023(14)
-0.246(16) 0.021(16) 0. 0. 0. 0. 0. 0. 0. 0. 0. 1.011(7) 0.950 2 3.176 2 3.176
2 3.176 3 3.176 4 3.176
H8 0.82(2) 0. 0. 0. 0.140(16) 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0.
0. 0. 0. 0. 0. 1.189(16) 1.163 2 2.000 1 2.000 2 2.000 3 2.000 4 2.000
O1W 6.25(7) 0. 0.117(15) 0.052(14) 0.123(15) -0.005(15) 0.089(15) 0.000(14)
0.053(15) 0.003(15) 0.020(13) -0.050(12) -0.012(11) 0.100(11) 0.064(12)
-0.044(11) -0.043(12) 0. 0. 0. 0. 0. 0. 0. 0. 0. 0.970(5) 0.984 2 4.466 2 4.466
2 4.466 3 4.466 4 4.466
H1W 0.90(4) 0. 0. 0. 0.211(18) 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0.
0. 0. 0. 0. 0. 1.12(3) 1.160 2 2.000 1 2.000 2 2.000 3 2.000 4 2.000
H2W 0.91(4) 0. 0. 0. 0.205(18) 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0.
0. 0. 0. 0. 0. 1.12(3) 1.160 2 2.000 1 2.000 2 2.000 3 2.000 4 2.000

loop_
_atom_local_axes_atom_label
_atom_local_axes_atom0
_atom_local_axes_ax1
_atom_local_axes_ax2
_atom_local_axes_atom1
_atom_local_axes_atom2
Br1 C2 bZ X Br1 O1W
N1 C6 bX Y N1 C2
N3 C4 bX Y N3 C2
N7 C8 bX Y N7 C5
N9 C4 bX Y N9 C8
O6 C6 X Y O6 N1
C1 N1 Z X C1 H12
H11 C1 Z X H11 N1
H12 C1 Z X H12 N1
H13 C1 Z X H13 N1
C2 N3 bX Y C2 N1
H2 C2 Z X H2 N3
C3 N3 Z X C3 H31
H31 C3 Z X H31 N3
H32 C3 Z X H32 N3
H33 C3 Z X H33 N3
C4 N3 bX Y C4 N9
C5 C6 bX Y C5 C4
C6 O6 bX Y C6 N1
C7 N7 Z X C7 H73
H71 C7 Z X H71 N7
H72 C7 Z X H72 N7
H73 C7 Z X H73 N7
C8 N7 bX Y C8 N9
H8 C8 Z X H8 N7
O1W Br1 bZ X O1W C3
H1W O1W Z X H1W C3
H2W O1W Z X H2W Br1




# start Validation Reply Form
_vrf_PLAT105_cmpnd_2Br_H2O_HR    
;
PROBLEM: CIF and RES Reported Wavelengths Inconsistent ..          ? Check 
RESPONSE: High resolution data was measured
to performed a charge density analysis,
using a multipolar model with MoPro 
program. Therefore, we embedded MoPro.par file
instead a shelxl.res file.
;
_vrf_PLAT230_cmpnd_2Br_H2O_HR    
;
PROBLEM: Hirshfeld Test Diff for    N7       --C7       .        7.9 s.u.  
RESPONSE: A careful analysis of Hirshfeld 
test shows a difference of mean-squares
amplitudes (DMSA) along interatomic vector
of 0.0014(3) A2, and therefore the discrepacy
corresponds to 4.3 s.u.

;
# end Validation Reply Form



