# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2024

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

data_tafz-a
_database_code_depnum_ccdc_archive 'CCDC 2308527'
loop_
_audit_author_name
_audit_author_address
'Ivan Fedyanin'
;Institute of Organoelement Compounds of Russian Academy of Sciences (INEOS RAS)
Russia
;
_audit_update_record             
;
2023-11-16 deposited with the CCDC.	2024-06-04 downloaded from the CCDC.
;

_publ_contact_name               'Fedyanin, Ivan V.'
_publ_contact_email              octy@xrlab.ineos.ac.ru

_audit_creation_method           'Modified SHELXL output'
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C2 N5 O, H4 N'
_chemical_formula_sum            'C2 H4 N6 O'
_chemical_formula_weight         128.11

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           53
_space_group_name_H-M_alt        'P m n a'
_space_group_name_Hall           '-P 2ac 2'

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

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

_cell_length_a                   12.1399(8)
_cell_length_b                   3.6287(3)
_cell_length_c                   11.6102(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     511.45(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    745
_cell_measurement_theta_min      3.36
_cell_measurement_theta_max      29.26

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.664
_exptl_crystal_F_000             264
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.137
_shelx_estimated_absorpt_T_min   0.969
_shelx_estimated_absorpt_T_max   0.976
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.773
_exptl_absorpt_correction_T_max  0.862
_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 Quest diffractometer'
_diffrn_detector_type            'Bruker PHOTON III CPAD area detector'
_diffrn_measurement_method       'ο scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4888
_diffrn_reflns_av_unetI/netI     0.0546
_diffrn_reflns_av_R_equivalents  0.0768
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.427
_diffrn_reflns_theta_max         30.050
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             781
_reflns_number_gt                650
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015b)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_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)+(0.0488P)²+0.2000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.066(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         781
_refine_ls_number_parameters     58
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0518
_refine_ls_R_factor_gt           0.0441
_refine_ls_wR_factor_ref         0.1116
_refine_ls_wR_factor_gt          0.1041
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.05813(13) 0.000000 0.500000 0.0156(4) Uani 1 2 d S T P . .
N2 N 0.09489(9) 0.0865(3) 0.39485(9) 0.0214(3) Uani 1 1 d D . . . .
N3 N 0.000000 0.163(7) 0.3401(8) 0.0186(18) Uani 0.5 2 d DS T P . .
O3 O 0.000000 0.120(6) 0.3267(6) 0.0186(18) Uani 0.5 2 d DS T P . .
C1' C 0.500000 0.9353(4) 0.44283(14) 0.0155(4) Uani 1 2 d S T P . .
N2' N 0.39616(8) 0.8931(3) 0.40652(9) 0.0206(3) Uani 1 1 d D . . . .
N3' N 0.3394(4) 1.000000 0.500000 0.0223(4) Uani 0.5 2 d DS T P . .
O3' O 0.3304(3) 1.000000 0.500000 0.0223(4) Uani 0.5 2 d DS T P . .
N1A N 0.250000 0.4866(4) 0.250000 0.0189(4) Uani 1 2 d S T P . .
H1 H 0.2077(14) 0.344(5) 0.3015(15) 0.034(5) Uiso 1 1 d . . . . .
H2 H 0.2014(14) 0.634(5) 0.2058(15) 0.034(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
C1 N2 1.3372(12) 4_556 ?
C1 N2 1.3372(12) . ?
C1 C1 1.411(3) 5_556 ?
N2 N3 1.344(3) . ?
N2 O3 1.403(3) . ?
C1' N2' 1.3381(12) . ?
C1' N2' 1.3381(12) 8_655 ?
C1' C1' 1.408(3) 5_676 ?
N2' N3' 1.343(3) . ?
N2' O3' 1.402(2) . ?
N1A H1 0.943(18) . ?
N1A H2 0.947(18) . ?
N1A H1 0.943(18) 3 ?
N1A H2 0.947(18) 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
N2 C1 N2 141.01(16) 4_556 . ?
N2 C1 C1 109.49(8) 4_556 5_556 ?
N2 C1 C1 109.50(8) . 5_556 ?
C1 N2 N3 101.2(2) . . ?
C1 N2 O3 105.16(16) . . ?
N2 N3 N2 118.0(4) 8 . ?
N2 O3 N2 110.4(3) 8 . ?
N2' C1' N2' 140.82(15) . 8_655 ?
N2' C1' C1' 109.59(8) . 5_676 ?
N2' C1' C1' 109.59(8) 8_655 5_676 ?
C1' N2' N3' 101.3(2) . . ?
C1' N2' O3' 105.11(16) . . ?
N2' N3' N2' 118.2(4) . 4_576 ?
N2' O3' N2' 110.6(3) . 4_576 ?
H1 N1A H2 108.3(15) . . ?
H1 N1A H1 113(2) . 3 ?
H2 N1A H1 107.8(15) . 3 ?
H1 N1A H2 107.8(15) . 3 ?
H2 N1A H2 111(2) . 3 ?
H1 N1A H2 108.3(15) 3 3 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N2 C1 N2 N3 -175.3(12) 4_556 . . . ?
C1 C1 N2 N3 4.7(12) 5_556 . . . ?
N2 C1 N2 O3 176.7(9) 4_556 . . . ?
C1 C1 N2 O3 -3.3(9) 5_556 . . . ?
C1 N2 N3 N2 -9(2) . . . 8 ?
O3 N2 N3 N2 109(8) . . . 8 ?
C1 N2 O3 N2 5.5(15) . . . 8 ?
N3 N2 O3 N2 -59(5) . . . 8 ?
N2' C1' N2' N3' 179.7(2) 8_655 . . . ?
C1' C1' N2' N3' 0.3(2) 5_676 . . . ?
N2' C1' N2' O3' 179.73(19) 8_655 . . . ?
C1' C1' N2' O3' 0.3(2) 5_676 . . . ?
C1' N2' N3' N2' -0.11(8) . . . 4_576 ?
O3' N2' N3' N2' 180.000(6) . . . 4_576 ?
C1' N2' O3' N2' -0.11(8) . . . 4_576 ?
N3' N2' O3' N2' 0.000(6) . . . 4_576 ?

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
_geom_hbond_publ_flag
N1A H1 N2 0.943(18) 1.981(18) 2.9123(13) 169.3(16) . yes
N1A H1 N3 0.943(18) 2.645(18) 3.419(7) 139.8(14) . yes
N1A H2 N2' 0.947(18) 1.997(18) 2.9370(13) 171.5(16) 3 yes

_refine_diff_density_max         0.460
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.080

####################################################################### 
# 
# 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_v30a
_database_code_depnum_ccdc_archive 'CCDC 2308531'
loop_
_audit_author_name
_audit_author_address
'Ivan Fedyanin'
;Institute of Organoelement Compounds of Russian Academy of Sciences (INEOS RAS)
Russia
;
_audit_update_record             
;
2023-11-16 deposited with the CCDC.	2024-06-04 downloaded from the CCDC.
;

_publ_contact_name               'Fedyanin, Ivan V.'
_publ_contact_email              octy@xrlab.ineos.ac.ru

_audit_creation_method           'Modified SHELXL output'
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C2 N7 O3, H4 N'
_chemical_formula_sum            'C2 H4 N8 O3'
_chemical_formula_weight         188.13

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   20.0924(5)
_cell_length_b                   5.83450(10)
_cell_length_c                   12.1652(3)
_cell_angle_alpha                90
_cell_angle_beta                 98.8230(10)
_cell_angle_gamma                90
_cell_volume                     1409.24(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6694
_cell_measurement_theta_min      3.39
_cell_measurement_theta_max      30.03

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.773
_exptl_crystal_F_000             768
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.159
_shelx_estimated_absorpt_T_min   0.958
_shelx_estimated_absorpt_T_max   0.969
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.830
_exptl_absorpt_correction_T_max  0.862
_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 Quest diffractometer'
_diffrn_detector_type            'Bruker PHOTON III CPAD area detector'
_diffrn_measurement_method       'ο scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10779
_diffrn_reflns_av_unetI/netI     0.0157
_diffrn_reflns_av_R_equivalents  0.0225
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.051
_diffrn_reflns_theta_max         29.976
_diffrn_reflns_theta_full        29.976
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             2023
_reflns_number_gt                1893
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015b)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_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)+(0.0426P)²+0.8861P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_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         2023
_refine_ls_number_parameters     134
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0310
_refine_ls_R_factor_gt           0.0293
_refine_ls_wR_factor_ref         0.0801
_refine_ls_wR_factor_gt          0.0790
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_restrained_S_all      1.074
_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 0.77245(4) 0.51615(13) 0.55624(6) 0.01428(16) Uani 1 1 d . . . . .
O2 O 0.81072(3) 0.35306(11) 0.62397(5) 0.01516(15) Uani 1 1 d . . . . .
O3 O 0.55705(3) 0.84555(11) 0.62810(6) 0.01771(15) Uani 1 1 d . . . . .
N3 N 0.77379(4) 0.22800(13) 0.69176(6) 0.01515(16) Uani 1 1 d . . . . .
C3A C 0.71300(4) 0.31341(14) 0.66458(7) 0.01160(16) Uani 1 1 d . . . . .
O4 O 0.46091(3) 0.66945(10) 0.62674(5) 0.01439(14) Uani 1 1 d . . . . .
N4 N 0.65040(4) 0.29095(12) 0.69317(6) 0.01201(15) Uani 1 1 d . . . . .
N5 N 0.61709(3) 0.45007(12) 0.62712(6) 0.01032(15) Uani 1 1 d . . . . .
N6 N 0.64857(3) 0.57242(12) 0.55780(6) 0.01199(15) Uani 1 1 d . . . . .
C6A C 0.71216(4) 0.48666(14) 0.58345(7) 0.01129(16) Uani 1 1 d . . . . .
N7 N 0.54872(3) 0.45431(12) 0.62843(6) 0.01215(15) Uani 1 1 d . . . . .
N8 N 0.52349(4) 0.66785(12) 0.62729(6) 0.01141(15) Uani 1 1 d . . . . .
N1A N 0.42688(4) 0.14864(12) 0.62541(6) 0.01158(15) Uani 1 1 d . . . . .
H1AD H 0.4340(7) -0.001(3) 0.6225(10) 0.020(3) Uiso 1 1 d . . . . .
H1AC H 0.4066(7) 0.179(2) 0.6822(11) 0.021(3) Uiso 1 1 d . . . . .
H1AB H 0.4653(7) 0.223(3) 0.6324(12) 0.024(3) Uiso 1 1 d . . . . .
H1AA H 0.4014(7) 0.191(2) 0.5653(12) 0.025(3) 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 C6A 1.3152(10) . ?
N1 O2 1.4075(9) . ?
O2 N3 1.3968(9) . ?
O3 N8 1.2360(9) . ?
N3 C3A 1.3137(11) . ?
C3A N4 1.3617(10) . ?
C3A C6A 1.4110(11) . ?
O4 N8 1.2565(9) . ?
N4 N5 1.3381(9) . ?
N5 N6 1.3357(9) . ?
N5 N7 1.3766(9) . ?
N6 C6A 1.3630(10) . ?
N7 N8 1.3443(10) . ?
N1A H1AD 0.887(15) . ?
N1A H1AC 0.873(14) . ?
N1A H1AB 0.879(15) . ?
N1A H1AA 0.863(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
C6A N1 O2 101.88(6) . . ?
N3 O2 N1 114.00(6) . . ?
C3A N3 O2 102.17(7) . . ?
N3 C3A N4 139.35(8) . . ?
N3 C3A C6A 111.02(7) . . ?
N4 C3A C6A 109.59(7) . . ?
N5 N4 C3A 100.15(6) . . ?
N6 N5 N4 120.55(7) . . ?
N6 N5 N7 124.59(7) . . ?
N4 N5 N7 114.43(6) . . ?
N5 N6 C6A 100.21(6) . . ?
N1 C6A N6 139.61(8) . . ?
N1 C6A C3A 110.92(7) . . ?
N6 C6A C3A 109.47(7) . . ?
N8 N7 N5 113.07(7) . . ?
O3 N8 O4 122.55(7) . . ?
O3 N8 N7 124.96(7) . . ?
O4 N8 N7 112.48(7) . . ?
H1AD N1A H1AC 109.4(12) . . ?
H1AD N1A H1AB 110.4(12) . . ?
H1AC N1A H1AB 109.3(13) . . ?
H1AD N1A H1AA 109.3(13) . . ?
H1AC N1A H1AA 108.8(13) . . ?
H1AB N1A H1AA 109.7(13) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6A N1 O2 N3 -0.43(9) . . . . ?
N1 O2 N3 C3A 0.56(9) . . . . ?
O2 N3 C3A N4 -177.83(10) . . . . ?
O2 N3 C3A C6A -0.45(9) . . . . ?
N3 C3A N4 N5 177.74(11) . . . . ?
C6A C3A N4 N5 0.34(8) . . . . ?
C3A N4 N5 N6 0.91(9) . . . . ?
C3A N4 N5 N7 173.74(7) . . . . ?
N4 N5 N6 C6A -1.72(9) . . . . ?
N7 N5 N6 C6A -173.78(7) . . . . ?
O2 N1 C6A N6 179.84(10) . . . . ?
O2 N1 C6A C3A 0.12(9) . . . . ?
N5 N6 C6A N1 -177.99(11) . . . . ?
N5 N6 C6A C3A 1.72(9) . . . . ?
N3 C3A C6A N1 0.23(10) . . . . ?
N4 C3A C6A N1 178.41(7) . . . . ?
N3 C3A C6A N6 -179.58(7) . . . . ?
N4 C3A C6A N6 -1.39(10) . . . . ?
N6 N5 N7 N8 -47.66(10) . . . . ?
N4 N5 N7 N8 139.84(7) . . . . ?
N5 N7 N8 O3 -1.92(12) . . . . ?
N5 N7 N8 O4 178.95(6) . . . . ?

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
_geom_hbond_publ_flag
N1A H1AD O4 0.887(15) 1.995(15) 2.8777(9) 173.1(12) 1_545 yes
N1A H1AC N4 0.873(14) 2.137(14) 3.0038(10) 172.0(12) 2_656 yes
N1A H1AB N7 0.879(15) 2.157(15) 3.0245(10) 168.9(13) . yes
N1A H1AA N6 0.863(15) 2.165(15) 2.9796(10) 157.3(13) 5_666 yes

_refine_diff_density_max         0.591
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.044

####################################################################### 
# 
# 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_tafz-hd-w
_database_code_depnum_ccdc_archive 'CCDC 2308529'
loop_
_audit_author_name
_audit_author_address
'Ivan Fedyanin'
;Institute of Organoelement Compounds of Russian Academy of Sciences (INEOS RAS)
Russia
;
_audit_update_record             
;
2023-11-16 deposited with the CCDC.	2024-06-04 downloaded from the CCDC.
;

_publ_contact_name               'Fedyanin, Ivan V.'
_publ_contact_email              octy@xrlab.ineos.ac.ru

_audit_creation_method           'Modified SHELXL output'
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C2 N5 O, H5 N2, H2 O'
_chemical_formula_sum            'C2 H7 N7 O2'
_chemical_formula_weight         161.15

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

_space_group_crystal_system      orthorhombic
_space_group_IT_number           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                   19.6742(16)
_cell_length_b                   3.7044(3)
_cell_length_c                   8.6710(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     631.95(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1544
_cell_measurement_theta_min      3.13
_cell_measurement_theta_max      30.41

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.694
_exptl_crystal_F_000             336
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.145
_shelx_estimated_absorpt_T_min   0.947
_shelx_estimated_absorpt_T_max   0.983
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.798
_exptl_absorpt_correction_T_max  0.862
_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 Quest diffractometer'
_diffrn_detector_type            'Bruker PHOTON III CPAD area detector'
_diffrn_measurement_method       'ο scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6092
_diffrn_reflns_av_unetI/netI     0.0558
_diffrn_reflns_av_R_equivalents  0.0576
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         4.143
_diffrn_reflns_theta_max         30.038
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measured_fraction_theta_full 0.971
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_Laue_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.945
_diffrn_reflns_point_group_measured_fraction_full 0.933
_reflns_number_total             1740
_reflns_number_gt                1618
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.814
_reflns_Friedel_fraction_max     0.905
_reflns_Friedel_fraction_full    0.889

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

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015b)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_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)+(0.0514P)²+0.0090P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_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_abs_structure_details .
_refine_ls_abs_structure_Flack   .
_chemical_absolute_configuration ?
_refine_ls_number_reflns         1740
_refine_ls_number_parameters     128
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0437
_refine_ls_R_factor_gt           0.0399
_refine_ls_wR_factor_ref         0.0960
_refine_ls_wR_factor_gt          0.0930
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_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
O1W O 0.74313(9) -0.0379(4) 0.8711(2) 0.0160(3) Uani 1 1 d . . . . .
N1 N 0.56808(10) 0.6670(5) 0.8493(2) 0.0159(4) Uani 1 1 d . . . . .
O2 O 0.51095(8) 0.8473(5) 0.79076(19) 0.0162(4) Uani 1 1 d . . . . .
N3 N 0.50956(9) 0.8562(5) 0.6285(2) 0.0159(4) Uani 1 1 d . . . . .
C3A C 0.56548(9) 0.6823(5) 0.5908(3) 0.0123(4) Uani 1 1 d . . . . .
N4 N 0.60206(10) 0.5793(5) 0.4652(2) 0.0138(4) Uani 1 1 d . . . . .
N5 N 0.65601(10) 0.4073(5) 0.5252(2) 0.0143(4) Uani 1 1 d . . . . .
N6 N 0.65779(10) 0.3898(5) 0.6799(2) 0.0145(4) Uani 1 1 d . . . . .
C6A C 0.60027(10) 0.5693(6) 0.7243(3) 0.0124(4) Uani 1 1 d . . . . .
N1H N 0.67954(9) 0.5620(5) 0.1304(2) 0.0137(4) Uani 1 1 d . . . . .
H1HA H 0.7114(16) 0.616(8) 0.199(5) 0.024(8) Uiso 1 1 d . . . . .
H1HB H 0.6969(17) 0.642(8) 0.035(4) 0.022(8) Uiso 1 1 d . . . . .
N2H N 0.62619(9) 0.8252(5) 0.1591(2) 0.0131(4) Uani 1 1 d . . . . .
H2HC H 0.5949(14) 0.785(8) 0.089(4) 0.018(7) Uiso 1 1 d . . . . .
H1WA H 0.769(2) 0.101(10) 0.912(5) 0.041(11) Uiso 1 1 d . . . . .
H1WB H 0.7165(19) 0.100(10) 0.811(4) 0.031(9) Uiso 1 1 d . . . . .
H2HB H 0.6113(13) 0.796(8) 0.252(4) 0.012(7) Uiso 1 1 d . . . . .
H2HA H 0.6418(14) 1.057(8) 0.154(3) 0.012(7) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1W H1WA 0.81(4) . ?
O1W H1WB 0.90(4) . ?
N1 C6A 1.307(3) . ?
N1 O2 1.402(2) . ?
O2 N3 1.408(2) . ?
N3 C3A 1.316(3) . ?
C3A N4 1.360(3) . ?
C3A C6A 1.408(3) . ?
N4 N5 1.343(3) . ?
N5 N6 1.343(2) . ?
N6 C6A 1.368(3) . ?
N1H N2H 1.454(2) . ?
N1H H1HA 0.89(4) . ?
N1H H1HB 0.94(4) . ?
N2H H2HC 0.88(3) . ?
N2H H2HB 0.87(3) . ?
N2H H2HA 0.91(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
H1WA O1W H1WB 105(3) . . ?
C6A N1 O2 102.71(17) . . ?
N1 O2 N3 112.86(15) . . ?
C3A N3 O2 102.72(17) . . ?
N3 C3A N4 141.1(2) . . ?
N3 C3A C6A 110.4(2) . . ?
N4 C3A C6A 108.52(18) . . ?
N5 N4 C3A 103.92(18) . . ?
N6 N5 N4 115.50(19) . . ?
N5 N6 C6A 103.65(18) . . ?
N1 C6A N6 140.3(2) . . ?
N1 C6A C3A 111.34(19) . . ?
N6 C6A C3A 108.39(19) . . ?
N2H N1H H1HA 104(2) . . ?
N2H N1H H1HB 101.5(19) . . ?
H1HA N1H H1HB 105(3) . . ?
N1H N2H H2HC 105.9(19) . . ?
N1H N2H H2HB 109(2) . . ?
H2HC N2H H2HB 113(3) . . ?
N1H N2H H2HA 112.4(18) . . ?
H2HC N2H H2HA 111(3) . . ?
H2HB N2H H2HA 106(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6A N1 O2 N3 -0.1(2) . . . . ?
N1 O2 N3 C3A 0.0(2) . . . . ?
O2 N3 C3A N4 -178.3(3) . . . . ?
O2 N3 C3A C6A 0.0(2) . . . . ?
N3 C3A N4 N5 179.2(3) . . . . ?
C6A C3A N4 N5 0.8(2) . . . . ?
C3A N4 N5 N6 -0.1(3) . . . . ?
N4 N5 N6 C6A -0.6(3) . . . . ?
O2 N1 C6A N6 -179.9(3) . . . . ?
O2 N1 C6A C3A 0.1(2) . . . . ?
N5 N6 C6A N1 -178.9(3) . . . . ?
N5 N6 C6A C3A 1.1(2) . . . . ?
N3 C3A C6A N1 -0.1(2) . . . . ?
N4 C3A C6A N1 178.8(2) . . . . ?
N3 C3A C6A N6 179.89(18) . . . . ?
N4 C3A C6A N6 -1.2(2) . . . . ?

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
_geom_hbond_publ_flag
N1H H1HA O1W 0.89(4) 2.16(4) 2.977(3) 153(3) 4_664 yes
N1H H1HB O1W 0.94(4) 2.06(3) 2.970(3) 161(3) 1_564 yes
N2H H2HC N1 0.88(3) 2.19(3) 2.978(3) 149(3) 1_554 yes
N2H H2HC N3 0.88(3) 2.47(3) 2.932(3) 113(2) 2_674 yes
O1W H1WA N5 0.81(4) 2.11(4) 2.906(3) 173(4) 4_655 yes
O1W H1WB N6 0.90(4) 1.95(4) 2.842(3) 179(4) . yes
N2H H2HB N4 0.87(3) 2.02(3) 2.846(3) 159(3) . yes

_refine_diff_density_max         0.390
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.048

####################################################################### 
# 
# 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_tafz-hd
_database_code_depnum_ccdc_archive 'CCDC 2308528'
loop_
_audit_author_name
_audit_author_address
'Ivan Fedyanin'
;Institute of Organoelement Compounds of Russian Academy of Sciences (INEOS RAS)
Russia
;
_audit_update_record             
;
2023-11-16 deposited with the CCDC.	2024-06-04 downloaded from the CCDC.
;

_publ_contact_name               'Fedyanin, Ivan V.'
_publ_contact_email              octy@xrlab.ineos.ac.ru

_audit_creation_method           'Modified SHELXL output'
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C2 N5 O, H5 N2'
_chemical_formula_sum            'C2 H5 N7 O'
_chemical_formula_weight         143.13

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

_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+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   14.1872(15)
_cell_length_b                   9.3706(7)
_cell_length_c                   8.6822(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1154.23(18)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1302
_cell_measurement_theta_min      2.60
_cell_measurement_theta_max      24.34

_exptl_crystal_description       shapeless
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.647
_exptl_crystal_F_000             592
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.136
_shelx_estimated_absorpt_T_min   0.964
_shelx_estimated_absorpt_T_max   0.973
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.652
_exptl_absorpt_correction_T_max  0.862
_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 Quest diffractometer'
_diffrn_detector_type            'Bruker PHOTON III CPAD area detector'
_diffrn_measurement_method       'ο scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15195
_diffrn_reflns_av_unetI/netI     0.0957
_diffrn_reflns_av_R_equivalents  0.1188
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.605
_diffrn_reflns_theta_max         28.015
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             2779
_reflns_number_gt                2122
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.873
_reflns_Friedel_fraction_max     0.992
_reflns_Friedel_fraction_full    0.995

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

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015b)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_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)+(0.0462P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_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_abs_structure_details .
_refine_ls_abs_structure_Flack   .
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2779
_refine_ls_number_parameters     221
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0791
_refine_ls_R_factor_gt           0.0550
_refine_ls_wR_factor_ref         0.1164
_refine_ls_wR_factor_gt          0.1046
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_restrained_S_all      1.008
_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 0.3205(2) 0.0573(3) 0.1023(4) 0.0240(7) Uani 1 1 d . . . . .
O2 O 0.2839(2) 0.0519(3) -0.0485(3) 0.0267(7) Uani 1 1 d . . . . .
N3 N 0.2712(2) 0.1882(3) -0.1131(4) 0.0239(7) Uani 1 1 d . . . . .
C3A C 0.3005(3) 0.2730(4) -0.0024(4) 0.0192(7) Uani 1 1 d . . . . .
N4 N 0.3112(2) 0.4155(3) 0.0293(4) 0.0219(7) Uani 1 1 d . . . . .
N5 N 0.3454(2) 0.4172(3) 0.1725(4) 0.0232(7) Uani 1 1 d . . . . .
N6 N 0.3575(2) 0.2879(3) 0.2376(4) 0.0214(7) Uani 1 1 d . . . . .
C6A C 0.3298(3) 0.1943(4) 0.1266(5) 0.0178(7) Uani 1 1 d . . . . .
N1' N 0.4197(3) 1.0128(3) 0.5693(4) 0.0291(8) Uani 1 1 d . . . . .
O2' O 0.4610(2) 1.0056(3) 0.4224(3) 0.0314(7) Uani 1 1 d . . . . .
N3' N 0.4816(2) 0.8645(4) 0.3765(4) 0.0263(8) Uani 1 1 d . . . . .
C3A' C 0.4522(3) 0.7908(4) 0.4962(4) 0.0196(7) Uani 1 1 d . . . . .
N4' N 0.4448(2) 0.6527(3) 0.5431(4) 0.0225(7) Uani 1 1 d . . . . .
N5' N 0.4053(2) 0.6614(3) 0.6833(4) 0.0235(7) Uani 1 1 d . . . . .
N6' N 0.3859(2) 0.7945(3) 0.7301(4) 0.0226(7) Uani 1 1 d . . . . .
C6A' C 0.4152(3) 0.8793(4) 0.6115(5) 0.0197(8) Uani 1 1 d . . . . .
N1H N 0.3884(2) 0.3296(4) 0.6278(4) 0.0190(7) Uani 1 1 d . . . . .
H1HA H 0.407(3) 0.259(4) 0.680(5) 0.016(11) Uiso 1 1 d . . . . .
H1HB H 0.386(3) 0.408(5) 0.679(5) 0.025(13) Uiso 1 1 d . . . . .
N2H N 0.4570(2) 0.3584(3) 0.5079(4) 0.0184(6) Uani 1 1 d . . . . .
H2HB H 0.461(3) 0.449(5) 0.499(5) 0.020(11) Uiso 1 1 d . . . . .
H2HA H 0.521(4) 0.320(5) 0.538(6) 0.051(15) Uiso 1 1 d . . . . .
H2HC H 0.434(3) 0.319(4) 0.417(5) 0.026(11) Uiso 1 1 d . . . . .
N1H' N 0.3652(2) 0.7417(3) 1.1124(4) 0.0186(7) Uani 1 1 d . . . . .
H1HD H 0.369(4) 0.838(6) 1.129(7) 0.054(16) Uiso 1 1 d . . . . .
H1HC H 0.348(3) 0.701(5) 1.201(6) 0.038(14) Uiso 1 1 d . . . . .
N2H' N 0.2891(2) 0.7199(3) 1.0043(4) 0.0192(7) Uani 1 1 d . . . . .
H2HD H 0.229(4) 0.760(4) 1.032(6) 0.041(13) Uiso 1 1 d . . . . .
H2HE H 0.307(3) 0.758(4) 0.910(6) 0.029(12) Uiso 1 1 d . . . . .
H2HF H 0.281(3) 0.627(5) 0.995(5) 0.029(12) 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 C6A 1.307(5) . ?
N1 O2 1.409(4) . ?
O2 N3 1.406(4) . ?
N3 C3A 1.315(5) . ?
C3A N4 1.371(4) . ?
C3A C6A 1.404(5) . ?
N4 N5 1.335(4) . ?
N5 N6 1.348(4) . ?
N6 C6A 1.362(5) . ?
N1' C6A' 1.305(5) . ?
N1' O2' 1.405(4) . ?
O2' N3' 1.411(5) . ?
N3' C3A' 1.316(5) . ?
C3A' N4' 1.360(5) . ?
C3A' C6A' 1.402(5) . ?
N4' N5' 1.342(4) . ?
N5' N6' 1.340(5) . ?
N6' C6A' 1.366(5) . ?
N1H N2H 1.451(4) . ?
N1H H1HA 0.84(4) . ?
N1H H1HB 0.86(4) . ?
N2H H2HB 0.86(4) . ?
N2H H2HA 1.01(6) . ?
N2H H2HC 0.93(5) . ?
N1H' N2H' 1.446(4) . ?
N1H' H1HD 0.91(5) . ?
N1H' H1HC 0.89(5) . ?
N2H' H2HD 0.97(5) . ?
N2H' H2HE 0.92(5) . ?
N2H' H2HF 0.88(5) . ?

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
C6A N1 O2 102.8(3) . . ?
N3 O2 N1 112.7(3) . . ?
C3A N3 O2 102.5(3) . . ?
N3 C3A N4 140.4(4) . . ?
N3 C3A C6A 111.0(3) . . ?
N4 C3A C6A 108.6(3) . . ?
N5 N4 C3A 103.8(3) . . ?
N4 N5 N6 115.3(3) . . ?
N5 N6 C6A 104.2(3) . . ?
N1 C6A N6 140.9(4) . . ?
N1 C6A C3A 110.9(3) . . ?
N6 C6A C3A 108.1(3) . . ?
C6A' N1' O2' 103.3(3) . . ?
N1' O2' N3' 112.8(3) . . ?
C3A' N3' O2' 101.7(3) . . ?
N3' C3A' N4' 139.5(4) . . ?
N3' C3A' C6A' 111.8(3) . . ?
N4' C3A' C6A' 108.7(3) . . ?
N5' N4' C3A' 104.2(3) . . ?
N6' N5' N4' 114.7(3) . . ?
N5' N6' C6A' 104.4(3) . . ?
N1' C6A' N6' 141.7(4) . . ?
N1' C6A' C3A' 110.4(3) . . ?
N6' C6A' C3A' 108.0(3) . . ?
N2H N1H H1HA 109(3) . . ?
N2H N1H H1HB 103(3) . . ?
H1HA N1H H1HB 114(4) . . ?
N1H N2H H2HB 107(3) . . ?
N1H N2H H2HA 111(3) . . ?
H2HB N2H H2HA 109(4) . . ?
N1H N2H H2HC 107(3) . . ?
H2HB N2H H2HC 110(4) . . ?
H2HA N2H H2HC 113(4) . . ?
N2H' N1H' H1HD 107(3) . . ?
N2H' N1H' H1HC 108(3) . . ?
H1HD N1H' H1HC 108(5) . . ?
N1H' N2H' H2HD 116(3) . . ?
N1H' N2H' H2HE 109(3) . . ?
H2HD N2H' H2HE 108(4) . . ?
N1H' N2H' H2HF 107(3) . . ?
H2HD N2H' H2HF 107(4) . . ?
H2HE N2H' H2HF 109(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6A N1 O2 N3 -0.3(4) . . . . ?
N1 O2 N3 C3A 0.4(4) . . . . ?
O2 N3 C3A N4 -179.6(5) . . . . ?
O2 N3 C3A C6A -0.3(4) . . . . ?
N3 C3A N4 N5 179.1(5) . . . . ?
C6A C3A N4 N5 -0.2(4) . . . . ?
C3A N4 N5 N6 -0.2(4) . . . . ?
N4 N5 N6 C6A 0.6(4) . . . . ?
O2 N1 C6A N6 178.7(5) . . . . ?
O2 N1 C6A C3A 0.1(4) . . . . ?
N5 N6 C6A N1 -179.4(5) . . . . ?
N5 N6 C6A C3A -0.7(4) . . . . ?
N3 C3A C6A N1 0.2(5) . . . . ?
N4 C3A C6A N1 179.7(3) . . . . ?
N3 C3A C6A N6 -178.9(3) . . . . ?
N4 C3A C6A N6 0.6(4) . . . . ?
C6A' N1' O2' N3' -0.1(4) . . . . ?
N1' O2' N3' C3A' 0.1(4) . . . . ?
O2' N3' C3A' N4' 178.5(5) . . . . ?
O2' N3' C3A' C6A' 0.0(4) . . . . ?
N3' C3A' N4' N5' -179.2(5) . . . . ?
C6A' C3A' N4' N5' -0.6(4) . . . . ?
C3A' N4' N5' N6' 0.5(4) . . . . ?
N4' N5' N6' C6A' -0.2(4) . . . . ?
O2' N1' C6A' N6' -179.2(5) . . . . ?
O2' N1' C6A' C3A' 0.1(4) . . . . ?
N5' N6' C6A' N1' 179.1(5) . . . . ?
N5' N6' C6A' C3A' -0.2(4) . . . . ?
N3' C3A' C6A' N1' 0.0(5) . . . . ?
N4' C3A' C6A' N1' -179.0(3) . . . . ?
N3' C3A' C6A' N6' 179.5(3) . . . . ?
N4' C3A' C6A' N6' 0.5(4) . . . . ?

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
_geom_hbond_publ_flag
N2H H2HB N4' 0.86(4) 1.96(4) 2.780(4) 161(4) . yes
N2H H2HA N1H' 1.01(6) 1.83(6) 2.841(5) 174(5) 2_664 yes
N2H H2HC N6 0.93(5) 1.92(5) 2.817(5) 161(4) . yes
N2H' H2HD N1H 0.97(5) 1.97(5) 2.922(5) 169(5) 4 yes
N2H' H2HE N5' 0.92(5) 2.58(5) 3.285(5) 133(3) . yes
N2H' H2HE N6' 0.92(5) 1.96(5) 2.836(5) 158(4) . yes
N2H' H2HF N4 0.88(5) 2.05(5) 2.878(4) 156(4) 1_556 yes
N1H' H1HD N1 0.91(5) 2.18(5) 3.026(4) 153(5) 1_566 yes
N1H' H1HC N3 0.89(5) 2.34(5) 3.111(5) 144(4) 4_556 yes
N1H H1HA N1' 0.84(4) 2.50(4) 3.045(5) 123(3) 1_545 yes
N1H H1HA N3' 0.84(4) 2.60(4) 3.373(5) 153(4) 2_665 yes
N1H H1HB N5' 0.86(4) 2.39(4) 3.156(5) 149(4) . yes

_refine_diff_density_max         0.266
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.052

