# Supplementary Information (SI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_ACS2_28-2-redo_auto
_database_code_depnum_ccdc_archive 'CCDC 2426284'
loop_
_audit_author_name
_audit_author_address
'Volodymyr Bon'
;Technische Universitaet Dresden
Germany
;
_audit_update_record             
;
2025-02-23 deposited with the CCDC.	2025-07-16 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT601_ACS2_28-2-redo_auto 
;
PROBLEM: Unit Cell Contains Solvent Accessible VOIDS of .        130 Ang**3
RESPONSE: The structure contains 1D channels, occupied by disordered guest
molecules, positions of which cannot be determined unambigiously.
;
# end Validation Reply Form



_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        Zn-bdp
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H8 N4 O11.20 Zn'
_chemical_formula_weight         452.79

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'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      tetragonal
_space_group_IT_number           131
_space_group_name_H-M_alt        'P 42/m m c'
_space_group_name_Hall           '-P 4c 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, -y, z'
'-y, x, z+1/2'
'y, -x, z+1/2'
'-x, y, -z'
'x, -y, -z'
'y, x, -z+1/2'
'-y, -x, -z+1/2'
'-x, -y, -z'
'x, y, -z'
'y, -x, -z-1/2'
'-y, x, -z-1/2'
'x, -y, z'
'-x, y, z'
'-y, -x, z-1/2'
'y, x, z-1/2'

_cell_length_a                   13.2864(2)
_cell_length_b                   13.2864(2)
_cell_length_c                   7.2865(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1286.27(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    9675
_cell_measurement_theta_min      3.0490
_cell_measurement_theta_max      29.7760

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.169
_exptl_crystal_F_000             455
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    1.002
_shelx_estimated_absorpt_T_min   0.889
_shelx_estimated_absorpt_T_max   0.924
_exptl_absorpt_correction_T_min  0.56994
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.132a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;

_oxdiff_exptl_absorpt_empirical_full_min 0.718
_oxdiff_exptl_absorpt_empirical_full_max 4.412
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_temperature      297(2)
_diffrn_ambient_environment      air
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, Eiger2 1M'
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            'Eiger2 1M'
_diffrn_detector_area_resol_mean 13.3333
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_reflns_number            14665
_diffrn_reflns_av_unetI/netI     0.0176
_diffrn_reflns_av_R_equivalents  0.0515
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.168
_diffrn_reflns_theta_max         29.746
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.933
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.933
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.933
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1001
_reflns_number_gt                821
_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_molecular_graphics    'Olex2 1.5-ac6-020 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac6-020 (Dolomanov et al., 2009)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_atom_sites_solution_primary     dual
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_data_collection       
'CrysAlisPro system (CCD 42.95a 64-bit (release 17-07-2023))'
_computing_cell_refinement       'CrysAlisPro 1.171.43.132a (Rigaku OD, 2024)'
_computing_data_reduction        'CrysAlisPro 1.171.43.132a (Rigaku OD, 2024)'
_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)+(0.0545P)²+0.0597P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1001
_refine_ls_number_parameters     36
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0349
_refine_ls_R_factor_gt           0.0290
_refine_ls_wR_factor_ref         0.0848
_refine_ls_wR_factor_gt          0.0821
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_restrained_S_all      1.102
_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
Zn01 Zn 0.500000 0.500000 0.750000 0.03179(15) Uani 1 8 d S T P . .
N002 N 0.500000 0.37833(9) 0.59260(15) 0.0444(3) Uani 1 2 d S T P . .
C003 C 0.500000 0.21736(16) 0.500000 0.0561(6) Uani 1 4 d S T P . .
C004 C 0.500000 0.10608(17) 0.500000 0.0644(7) Uani 1 4 d S T P . .
C005 C 0.500000 0.28183(12) 0.6475(2) 0.0611(5) Uani 1 2 d S T P . .
H005 H 0.500000 0.261298 0.769534 0.073 Uiso 1 2 calc R U P . .
C006 C 0.500000 0.05217(13) 0.3403(3) 0.1024(10) Uani 1 2 d S T P . .
H006 H 0.500000 0.086308 0.228851 0.123 Uiso 1 2 calc R U P . .
O1 O 0.8215(19) 0.2543(18) 0.500000 0.709(14) Uiso 1 2 d S . P . .
O2 O 0.1788(11) 0.1884(9) 0.852(2) 0.614(10) Uiso 0.9 1 d . . P . .


_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
Zn01 N002 1.9821(11) . ?
Zn01 N002 1.9821(11) 12_657 ?
Zn01 N002 1.9821(11) 2_665 ?
Zn01 N002 1.9821(11) 11_567 ?
N002 C005 1.3431(18) . ?
N002 N002 1.349(2) 10_556 ?
C003 C005 1.374(2) . ?
C003 C005 1.374(2) 10_556 ?
C003 C004 1.479(3) . ?
C004 C006 1.367(2) 10_556 ?
C004 C006 1.367(2) . ?
C006 C006 1.386(4) 2_655 ?
O1 O2 1.48(2) 3_654 ?
O1 O2 1.48(2) 12_657 ?
O2 O2 1.49(3) 7_556 ?

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
N002 Zn01 N002 109.56(3) . 12_657 ?
N002 Zn01 N002 109.29(7) . 2_665 ?
N002 Zn01 N002 109.56(3) 12_657 2_665 ?
N002 Zn01 N002 109.56(3) . 11_567 ?
N002 Zn01 N002 109.29(7) 12_657 11_567 ?
N002 Zn01 N002 109.56(3) 2_665 11_567 ?
C005 N002 N002 107.33(9) . 10_556 ?
C005 N002 Zn01 127.31(10) . . ?
N002 N002 Zn01 125.36(3) 10_556 . ?
C005 C003 C005 102.9(2) . 10_556 ?
C005 C003 C004 128.55(10) . . ?
C005 C003 C004 128.55(10) 10_556 . ?
C006 C004 C006 116.8(2) 10_556 . ?
C006 C004 C003 121.61(12) 10_556 . ?
C006 C004 C003 121.61(12) . . ?
N002 C005 C003 111.22(15) . . ?
C004 C006 C006 121.61(12) . 2_655 ?
O2 O1 O2 93.7(19) 3_654 12_657 ?
O1 O2 O2 131.2(14) 11_567 7_556 ?

_refine_diff_density_max         0.253
_refine_diff_density_min         -0.274
_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_ACS4_16-BUT-1_auto
_database_code_depnum_ccdc_archive 'CCDC 2426285'
loop_
_audit_author_name
_audit_author_address
'Volodymyr Bon'
;Technische Universitaet Dresden
Germany
;
_audit_update_record             
;
2025-02-23 deposited with the CCDC.	2025-07-16 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT601_ACS4_16-BUT-1_auto  
;
PROBLEM: Unit Cell Contains Solvent Accessible VOIDS of .        579 Ang**3
RESPONSE: The structure contains 1D channels, occupied by disordered guest
molecules, positions of which cannot be determined unambigiously.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        BUT-58
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H8 N4 O0.50 Zn'
_chemical_formula_weight         281.59

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'
Zn Zn 0.2839 1.4301 '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      tetragonal
_space_group_IT_number           98
_space_group_name_H-M_alt        'I 41 2 2'
_space_group_name_Hall           'I 4bw 2bw'

_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'
'-y, x+1/2, z+1/4'
'y+1/2, -x, z+3/4'
'-x+1/2, y, -z+3/4'
'x, -y+1/2, -z+1/4'
'y+1/2, x+1/2, -z+1/2'
'-y, -x, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, -y+1, z+1'
'-y+1/2, x+1, z+3/4'
'y+1, -x+1/2, z+5/4'
'-x+1, y+1/2, -z+5/4'
'x+1/2, -y+1, -z+3/4'
'y+1, x+1, -z+1'
'-y+1/2, -x+1/2, -z+1/2'

_cell_length_a                   16.3434(2)
_cell_length_b                   16.3434(2)
_cell_length_c                   12.5154(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3342.95(10)
_cell_formula_units_Z            8
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    17415
_cell_measurement_theta_min      2.4970
_cell_measurement_theta_max      29.6060


_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.119
_exptl_crystal_F_000             1136
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    1.459
_shelx_estimated_absorpt_T_min   0.844
_shelx_estimated_absorpt_T_max   0.892
_exptl_absorpt_correction_T_min  0.81539
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.95a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.871
_oxdiff_exptl_absorpt_empirical_full_max 1.242
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_temperature      297(2)
_diffrn_ambient_environment      air
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, Eiger2 1M'
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            'Eiger2 1M'
_diffrn_detector_area_resol_mean 13.3333
_diffrn_reflns_number            22684
_diffrn_reflns_av_unetI/netI     0.0139
_diffrn_reflns_av_R_equivalents  0.0319
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.492
_diffrn_reflns_theta_max         29.736
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.938
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.938
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.917
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2204
_reflns_number_gt                2083
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.697
_reflns_Friedel_fraction_max     0.889
_reflns_Friedel_fraction_full    1.000

_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       'CrysAlisPro 1.171.42.95a (Rigaku OD, 2023)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.95a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.95a (Rigaku OD, 2023)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0916P)²+0.0326P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 826 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.009(6)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2204
_refine_ls_number_parameters     79
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0339
_refine_ls_R_factor_gt           0.0320
_refine_ls_wR_factor_ref         0.1179
_refine_ls_wR_factor_gt          0.1167
_refine_ls_goodness_of_fit_ref   1.128
_refine_ls_restrained_S_all      1.128
_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
Zn1 Zn 0.250000 0.67613(3) 0.875000 0.03128(19) Uani 1 2 d S T P . .
N5 N 0.26692(17) 0.61676(16) 0.7394(2) 0.0391(6) Uani 1 1 d . . . . .
N4 N 0.24117(18) 0.64734(17) 0.6448(2) 0.0380(6) Uani 1 1 d . . . . .
C6 C 0.3123(3) 0.5498(2) 0.7187(3) 0.0495(9) Uani 1 1 d . . . . .
H6 H 0.337200 0.517519 0.770609 0.059 Uiso 1 1 calc R U . . .
C3 C 0.2707(2) 0.5987(2) 0.5669(3) 0.0466(8) Uani 1 1 d . . . . .
H3 H 0.261501 0.606321 0.494274 0.056 Uiso 1 1 calc R U . . .
C2 C 0.3169(2) 0.5354(2) 0.6102(3) 0.0451(7) Uani 1 1 d . . . . .
C7 C 0.3655(2) 0.4732(2) 0.5538(3) 0.0481(8) Uani 1 1 d . . . . .
C9 C 0.4175(4) 0.4208(4) 0.6093(3) 0.0802(16) Uani 1 1 d . . . . .
H9 H 0.415470 0.420324 0.683539 0.096 Uiso 1 1 calc R U . . .
C8 C 0.4722(4) 0.3693(3) 0.5581(4) 0.0763(17) Uani 1 1 d . . . . .
H8 H 0.508188 0.337347 0.597795 0.092 Uiso 1 1 calc R U . . .
O1 O 0.500000 0.500000 1.000000 0.50(2) Uiso 1 4 d S . P . .


_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
Zn1 N5 1.974(3) . ?
Zn1 N5 1.974(3) 5_556 ?
Zn1 N4 2.002(3) 3_655 ?
Zn1 N4 2.002(3) 7_456 ?
N5 N4 1.352(4) . ?
N5 C6 1.348(4) . ?
N4 C3 1.348(4) . ?
C6 C2 1.380(5) . ?
C3 C2 1.390(5) . ?
C2 C7 1.471(5) . ?
C7 C9 1.392(6) . ?
C7 C8 1.402(5) 15_445 ?
C9 C8 1.385(6) . ?

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
N5 Zn1 N5 121.11(17) . 5_556 ?
N5 Zn1 N4 104.49(11) . 3_655 ?
N5 Zn1 N4 105.78(11) 5_556 3_655 ?
N5 Zn1 N4 105.78(11) . 7_456 ?
N5 Zn1 N4 104.49(11) 5_556 7_456 ?
N4 Zn1 N4 115.85(17) 3_655 7_456 ?
N4 N5 C6 107.7(3) . . ?
N4 N5 Zn1 121.81(19) . . ?
C6 N5 Zn1 129.9(3) . . ?
C3 N4 N5 107.7(3) . . ?
C3 N4 Zn1 126.5(2) . 4_464 ?
N5 N4 Zn1 125.71(18) . 4_464 ?
N5 C6 C2 110.9(3) . . ?
N4 C3 C2 110.6(3) . . ?
C6 C2 C3 103.2(3) . . ?
C6 C2 C7 128.2(4) . . ?
C3 C2 C7 128.3(3) . . ?
C9 C7 C8 117.7(4) . 15_445 ?
C9 C7 C2 121.1(4) . . ?
C8 C7 C2 120.7(4) 15_445 . ?
C8 C9 C7 122.5(3) . . ?
C9 C8 C7 119.7(4) . 15_445 ?

_refine_diff_density_max         0.544
_refine_diff_density_min         -0.291
_refine_diff_density_rms         0.113



####################################################################### 
# 
# 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_Imma_a
_database_code_depnum_ccdc_archive 'CCDC 2426286'
loop_
_audit_author_name
_audit_author_address
'Volodymyr Bon'
;Technische Universitaet Dresden
Germany
;
_audit_update_record             
;
2025-02-23 deposited with the CCDC.	2025-07-16 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT430_Imma_a              
;
PROBLEM: Short Inter D...A Contact  O1       ..O2       .       2.13 Ang.  
RESPONSE: Both atoms show elongated thermal ellipsoid, indicating the disorder.
Most probably O2 is the part of disordered molecule, which cannot be modelled
completely 
;
_vrf_PLAT601_Imma_a              
;
PROBLEM: Unit Cell Contains Solvent Accessible VOIDS   <=        618 Ang**3
RESPONSE: The structure is porous showing 1D channels filled with disordered solvent
molecules.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        Ni-bdp
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H8 N4 Ni O2'
_chemical_formula_weight         298.93

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0040 0.0020 '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 0.0080 0.0040 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0130 0.0070 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni 0.3260 1.3020 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           74
_space_group_name_H-M_alt        'I m m a'
_space_group_name_Hall           '-I 2b 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, -y+1/2, z'
'-x, y+1/2, -z'
'x, -y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, -y+1, z+1/2'
'-x+1/2, y+1, -z+1/2'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x, y-1/2, -z'
'x, -y-1/2, z'
'-x, y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x+1/2, y, -z+1/2'
'x+1/2, -y, z+1/2'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   22.000(4)
_cell_length_b                   6.9300(14)
_cell_length_c                   14.760(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2250.3(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    687
_cell_measurement_theta_min      3.86
_cell_measurement_theta_max      24.24


_exptl_crystal_description       stick
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    0.882
_exptl_crystal_F_000             608
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    1.088
_shelx_estimated_absorpt_T_min   0.837
_shelx_estimated_absorpt_T_max   0.899
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.7749
_diffrn_radiation_type           synchrotron
_diffrn_source                   'BESSY BL MX-14.2'
_diffrn_measurement_device_type  'Pilatus 2M'
_diffrn_measurement_method       'Δφ scans'
_diffrn_reflns_number            8438
_diffrn_reflns_av_unetI/netI     0.0244
_diffrn_reflns_av_R_equivalents  0.0335
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.811
_diffrn_reflns_theta_max         32.994
_diffrn_reflns_theta_full        27.706
_diffrn_measured_fraction_theta_max 0.905
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.905
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.905
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             1637
_reflns_number_gt                1442
_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       mxcube
_computing_cell_refinement       mxcube
_computing_data_reduction        'XDSAPP 3.0'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1443P)²+0.8283P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1637
_refine_ls_number_parameters     52
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0691
_refine_ls_R_factor_gt           0.0660
_refine_ls_wR_factor_ref         0.2120
_refine_ls_wR_factor_gt          0.2059
_refine_ls_goodness_of_fit_ref   1.206
_refine_ls_restrained_S_all      1.206
_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
Ni1 Ni 0.500000 0.500000 0.500000 0.0350(3) Uani 1 4 d S T P . .
N1 N 0.43816(7) 0.3471(3) 0.44295(13) 0.0445(5) Uani 1 1 d . . . . .
C2 C 0.35792(14) 0.250000 0.3620(3) 0.0529(8) Uani 1 2 d S T P . .
C1 C 0.39003(11) 0.4062(4) 0.3951(2) 0.0553(6) Uani 1 1 d . . . . .
H1 H 0.379603 0.534637 0.385451 0.066 Uiso 1 1 calc R U . . .
C3 C 0.30279(15) 0.250000 0.3049(3) 0.0587(9) Uani 1 2 d S T P . .
C4 C 0.27604(19) 0.0834(5) 0.2766(4) 0.1157(19) Uani 1 1 d . . . . .
H4 H 0.293159 -0.033940 0.293393 0.139 Uiso 1 1 calc R U . . .
O1 O 0.500000 0.250000 0.6187(7) 0.216(7) Uani 1 4 d S T P . .
O2 O 0.500000 0.250000 0.7631(19) 0.40(2) Uani 1 4 d S T P . .


_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
Ni1 N1 1.9189(17) 9_666 ?
Ni1 N1 1.9189(17) 12_655 ?
Ni1 N1 1.9189(17) 4_566 ?
Ni1 N1 1.9190(17) . ?
N1 C1 1.337(3) . ?
N1 N1 1.346(4) 11_565 ?
C2 C1 1.382(3) . ?
C2 C1 1.382(3) 11_565 ?
C2 C3 1.477(4) . ?
C1 H1 0.9300 . ?
C3 C4 1.361(4) 11_565 ?
C3 C4 1.361(4) . ?
C4 C4 1.389(5) 7_545 ?
C4 H4 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Ni1 N1 89.69(10) 9_666 12_655 ?
N1 Ni1 N1 90.31(10) 9_666 4_566 ?
N1 Ni1 N1 180.0 12_655 4_566 ?
N1 Ni1 N1 180.0 9_666 . ?
N1 Ni1 N1 90.31(10) 12_655 . ?
N1 Ni1 N1 89.69(10) 4_566 . ?
C1 N1 N1 107.84(13) . 11_565 ?
C1 N1 Ni1 128.63(16) . . ?
N1 N1 Ni1 123.50(5) 11_565 . ?
C1 C2 C1 103.1(3) . 11_565 ?
C1 C2 C3 128.43(14) . . ?
C1 C2 C3 128.43(14) 11_565 . ?
N1 C1 C2 110.6(2) . . ?
N1 C1 H1 124.7 . . ?
C2 C1 H1 124.7 . . ?
C4 C3 C4 116.0(3) 11_565 . ?
C4 C3 C2 122.01(17) 11_565 . ?
C4 C3 C2 122.00(17) . . ?
C3 C4 C4 122.00(17) . 7_545 ?
C3 C4 H4 119.0 . . ?
C4 C4 H4 119.0 7_545 . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 N1 C1 C2 -0.7(3) 11_565 . . . ?
Ni1 N1 C1 C2 177.3(2) . . . . ?
C1 C2 C1 N1 1.0(4) 11_565 . . . ?
C3 C2 C1 N1 -178.8(4) . . . . ?
C1 C2 C3 C4 0.2(8) . . . 11_565 ?
C1 C2 C3 C4 -179.6(5) 11_565 . . 11_565 ?
C1 C2 C3 C4 179.6(5) . . . . ?
C1 C2 C3 C4 -0.2(8) 11_565 . . . ?
C4 C3 C4 C4 -1.1(13) 11_565 . . 7_545 ?
C2 C3 C4 C4 179.5(7) . . . 7_545 ?

_refine_diff_density_max         0.790
_refine_diff_density_min         -0.928
_refine_diff_density_rms         0.203



