# Supplementary Information (SI) for CrystEngComm.
# 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_526s_tw
_database_code_depnum_ccdc_archive 'CCDC 2408082'
loop_
_audit_author_name
_audit_author_address
'Galina Romanenko'
;International Tomography Center
Russia
;
_audit_update_record             
;
2024-12-05 deposited with the CCDC.	2025-10-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H12 Co N12 O10'
_chemical_formula_weight         495.23

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'
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'
Co Co 0.3494 0.9721 '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'

_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                   9.2929(7)
_cell_length_b                   6.5584(4)
_cell_length_c                   14.4252(8)
_cell_angle_alpha                90
_cell_angle_beta                 95.720(4)
_cell_angle_gamma                90
_cell_volume                     874.79(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2711
_cell_measurement_theta_min      2.50
_cell_measurement_theta_max      27.37

_exptl_crystal_description       plate
_exptl_crystal_colour            black
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.880
_exptl_crystal_F_000             502
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.02
_exptl_absorpt_coefficient_mu    1.068
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.2373
_exptl_absorpt_correction_T_max  0.2906
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(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            2753
_diffrn_reflns_av_unetI/netI     0.0653
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.498
_diffrn_reflns_theta_max         31.729
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.927
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.927
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.927
_diffrn_reflns_point_group_measured_fraction_full 0.987
_reflns_number_total             2753
_reflns_number_gt                1775
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 _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. Completness statistics refer to single and 
 composite reflections containing twin component 1 only. 
;

_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-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
; 
 Refined as a 2-component twin. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0595P)²] 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         2753
_refine_ls_number_parameters     167
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0758
_refine_ls_R_factor_gt           0.0482
_refine_ls_wR_factor_ref         0.1163
_refine_ls_wR_factor_gt          0.1069
_refine_ls_goodness_of_fit_ref   0.940
_refine_ls_restrained_S_all      0.941
_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
Co Co 0.000000 0.000000 0.000000 0.02585(15) Uani 1 2 d S . P . .
O1 O 0.2810(2) 0.4998(3) 0.20167(14) 0.0457(5) Uani 1 1 d . . . . .
N2 N 0.1876(2) 0.3853(4) 0.14058(15) 0.0398(5) Uani 1 1 d . . . . .
C3 C 0.2634(2) 0.2227(4) 0.12304(14) 0.0261(5) Uani 1 1 d . . . . .
N4 N 0.2164(2) 0.0628(3) 0.06866(12) 0.0275(4) Uani 1 1 d . . . . .
C5 C 0.3243(3) -0.0756(4) 0.06717(15) 0.0282(5) Uani 1 1 d . . . . .
N6 N 0.3157(2) -0.2485(3) 0.02080(16) 0.0419(5) Uani 1 1 d . . . . .
O7 O 0.4502(2) -0.3374(3) 0.04164(14) 0.0532(5) Uani 1 1 d . . . . .
N8 N 0.5431(2) -0.2208(4) 0.10115(17) 0.0482(6) Uani 1 1 d . . . . .
C9 C 0.4666(3) -0.0573(4) 0.11796(17) 0.0317(5) Uani 1 1 d . . . . .
N10 N 0.5119(2) 0.0981(4) 0.17353(14) 0.0346(5) Uani 1 1 d . . . . .
C11 C 0.4065(2) 0.2375(4) 0.17371(15) 0.0287(5) Uani 1 1 d . . . . .
N12 N 0.4151(2) 0.4088(4) 0.22155(14) 0.0405(5) Uani 1 1 d . . . . .
O1W O 0.0960(2) -0.0941(4) -0.11956(13) 0.0383(5) Uani 1 1 d . . . . .
H11 H 0.133(4) -0.203(6) -0.124(2) 0.061(11) Uiso 1 1 d . . . . .
H12 H 0.055(4) -0.064(5) -0.165(3) 0.056(11) Uiso 1 1 d . . . . .
O2W O 0.0010(2) -0.2891(3) 0.05362(14) 0.0390(5) Uani 1 1 d D . . . .
H21 H 0.067(3) -0.352(5) 0.053(2) 0.046(10) Uiso 1 1 d . . . . .
H22 H -0.073(3) -0.342(5) 0.092(2) 0.089(13) Uiso 1 1 d D . . . .
O11W O -0.1898(2) -0.4779(3) 0.15665(15) 0.0492(6) Uani 1 1 d D . . . .
H112 H -0.158(5) -0.424(8) 0.217(2) 0.139(19) Uiso 1 1 d D . . . .
H111 H -0.288(2) -0.432(7) 0.145(3) 0.109(15) Uiso 1 1 d 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
Co O2W 2.0474(19) 3 ?
Co O2W 2.0474(19) . ?
Co O1W 2.1116(18) . ?
Co O1W 2.1116(18) 3 ?
Co N4 2.1907(19) . ?
Co N4 2.1907(19) 3 ?
O1 N12 1.386(3) . ?
O1 N2 1.393(3) . ?
N2 C3 1.317(3) . ?
C3 N4 1.356(3) . ?
C3 C11 1.455(3) . ?
N4 C5 1.354(3) . ?
C5 N6 1.315(3) . ?
C5 C9 1.452(3) . ?
N6 O7 1.385(3) . ?
O7 N8 1.385(3) . ?
N8 C9 1.322(3) . ?
C9 N10 1.339(4) . ?
N10 C11 1.340(3) . ?
C11 N12 1.317(3) . ?
O1W H11 0.80(4) . ?
O1W H12 0.75(4) . ?
O2W H21 0.74(3) . ?
O2W H22 0.987(18) . ?
O11W H112 0.956(19) . ?
O11W H111 0.961(14) . ?

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
O2W Co O2W 180.0 3 . ?
O2W Co O1W 87.04(9) 3 . ?
O2W Co O1W 92.95(9) . . ?
O2W Co O1W 92.96(9) 3 3 ?
O2W Co O1W 87.05(9) . 3 ?
O1W Co O1W 180.00(5) . 3 ?
O2W Co N4 88.07(8) 3 . ?
O2W Co N4 91.93(8) . . ?
O1W Co N4 88.88(7) . . ?
O1W Co N4 91.12(7) 3 . ?
O2W Co N4 91.93(8) 3 3 ?
O2W Co N4 88.07(8) . 3 ?
O1W Co N4 91.12(7) . 3 ?
O1W Co N4 88.88(7) 3 3 ?
N4 Co N4 180.0 . 3 ?
N12 O1 N2 112.94(18) . . ?
C3 N2 O1 104.26(19) . . ?
N2 C3 N4 126.2(2) . . ?
N2 C3 C11 109.2(2) . . ?
N4 C3 C11 124.6(2) . . ?
C3 N4 C5 109.36(19) . . ?
C3 N4 Co 129.44(15) . . ?
C5 N4 Co 120.98(17) . . ?
N6 C5 N4 125.3(2) . . ?
N6 C5 C9 109.5(2) . . ?
N4 C5 C9 125.1(2) . . ?
C5 N6 O7 104.2(2) . . ?
N8 O7 N6 113.28(18) . . ?
C9 N8 O7 104.4(2) . . ?
N8 C9 N10 125.8(2) . . ?
N8 C9 C5 108.7(2) . . ?
N10 C9 C5 125.5(2) . . ?
C9 N10 C11 109.6(2) . . ?
N12 C11 N10 125.2(2) . . ?
N12 C11 C3 109.0(2) . . ?
N10 C11 C3 125.8(2) . . ?
C11 N12 O1 104.60(19) . . ?
Co O1W H11 123(2) . . ?
Co O1W H12 114(3) . . ?
H11 O1W H12 111(3) . . ?
Co O2W H21 119(2) . . ?
Co O2W H22 124(2) . . ?
H21 O2W H22 116(3) . . ?
H112 O11W H111 104(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
N12 O1 N2 C3 0.4(3) . . . . ?
O1 N2 C3 N4 178.0(2) . . . . ?
O1 N2 C3 C11 -0.4(3) . . . . ?
N2 C3 N4 C5 -179.9(2) . . . . ?
C11 C3 N4 C5 -1.8(3) . . . . ?
N2 C3 N4 Co -5.4(4) . . . . ?
C11 C3 N4 Co 172.78(17) . . . . ?
C3 N4 C5 N6 -179.7(2) . . . . ?
Co N4 C5 N6 5.2(3) . . . . ?
C3 N4 C5 C9 1.5(3) . . . . ?
Co N4 C5 C9 -173.59(18) . . . . ?
N4 C5 N6 O7 -179.2(2) . . . . ?
C9 C5 N6 O7 -0.2(3) . . . . ?
C5 N6 O7 N8 0.1(3) . . . . ?
N6 O7 N8 C9 0.0(3) . . . . ?
O7 N8 C9 N10 179.0(2) . . . . ?
O7 N8 C9 C5 -0.1(3) . . . . ?
N6 C5 C9 N8 0.2(3) . . . . ?
N4 C5 C9 N8 179.2(2) . . . . ?
N6 C5 C9 N10 -178.9(2) . . . . ?
N4 C5 C9 N10 0.1(4) . . . . ?
N8 C9 N10 C11 179.6(2) . . . . ?
C5 C9 N10 C11 -1.3(3) . . . . ?
C9 N10 C11 N12 179.6(2) . . . . ?
C9 N10 C11 C3 1.0(3) . . . . ?
N2 C3 C11 N12 0.2(3) . . . . ?
N4 C3 C11 N12 -178.2(2) . . . . ?
N2 C3 C11 N10 179.0(2) . . . . ?
N4 C3 C11 N10 0.6(4) . . . . ?
N10 C11 N12 O1 -178.7(2) . . . . ?
C3 C11 N12 O1 0.0(3) . . . . ?
N2 O1 N12 C11 -0.3(3) . . . . ?

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
O1W H11 N6 0.80(4) 2.57(3) 2.910(3) 107(3) . yes
O1W H11 O11W 0.80(4) 2.22(4) 3.003(3) 167(3) 3_545 yes
O1W H12 N12 0.75(4) 2.24(4) 2.964(3) 166(3) 4_565 yes
O2W H21 N2 0.74(3) 2.35(3) 2.951(3) 139(3) 1_545 yes
O2W H21 N6 0.74(3) 2.49(3) 3.020(3) 129(3) . yes
O2W H22 O11W 0.987(18) 1.75(2) 2.722(3) 169(3) . yes
O11W H112 N10 0.956(19) 1.98(3) 2.859(3) 151(4) 2_545 yes
O11W H111 N8 0.961(14) 2.14(2) 3.041(3) 156(4) 1_455 yes

_refine_diff_density_max         0.854
_refine_diff_density_min         -0.627
_refine_diff_density_rms         0.101


# start Validation Reply Form
_vrf_PLAT430_526s_tw             
;
PROBLEM: Short Inter D...A Contact O7 ..O7 . 2.66 Ang.
RESPONSE: Specific intermolecular contact
;
# end Validation Reply Form
####################################################################### 
# 
# 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_515
_database_code_depnum_ccdc_archive 'CCDC 2408084'
loop_
_audit_author_name
_audit_author_address
'Galina Romanenko'
;International Tomography Center
Russia
;
_audit_update_record             
;
2024-12-05 deposited with the CCDC.	2025-10-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H12 Cu N16 O4'
_chemical_formula_weight         459.88

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 '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                   8.3743(3)
_cell_length_b                   10.4991(4)
_cell_length_c                   9.5646(4)
_cell_angle_alpha                90
_cell_angle_beta                 108.1066(18)
_cell_angle_gamma                90
_cell_volume                     799.30(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5083
_cell_measurement_theta_min      6.15
_cell_measurement_theta_max      67.53

_exptl_crystal_description       prism
_exptl_crystal_colour            black
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.911
_exptl_crystal_F_000             466
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.005
_exptl_absorpt_coefficient_mu    2.547
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_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     1.54178
_diffrn_radiation_type           CuK\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            7965
_diffrn_reflns_av_unetI/netI     0.0242
_diffrn_reflns_av_R_equivalents  0.0306
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         6.147
_diffrn_reflns_theta_max         67.556
_diffrn_reflns_theta_full        67.556
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             1439
_reflns_number_gt                1362
_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-2018/3 (Sheldrick, 2018)'
_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)+(0.0605P)²+0.1707P] 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         1439
_refine_ls_number_parameters     157
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0313
_refine_ls_R_factor_gt           0.0300
_refine_ls_wR_factor_ref         0.0866
_refine_ls_wR_factor_gt          0.0849
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_restrained_S_all      1.085
_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
Cu Cu 0.500000 -0.500000 0.500000 0.03432(17) Uani 1 2 d S . P . .
O1 O 0.1835(2) -0.57935(16) 0.87305(16) 0.0570(4) Uani 1 1 d . . . . .
N2 N 0.2662(2) -0.57337(16) 0.76721(18) 0.0449(4) Uani 1 1 d . . . . .
C3 C 0.1915(2) -0.47907(16) 0.68103(19) 0.0304(4) Uani 1 1 d . . . . .
N4 N 0.22952(16) -0.43832(13) 0.56115(15) 0.0303(3) Uani 1 1 d . . . . .
C5 C 0.12641(19) -0.34203(15) 0.49892(17) 0.0287(3) Uani 1 1 d . . . . .
N6 N 0.12699(19) -0.27979(15) 0.37889(17) 0.0402(4) Uani 1 1 d . . . . .
O7 O -0.00184(18) -0.19093(14) 0.35747(16) 0.0500(4) Uani 1 1 d . . . . .
N8 N -0.0831(2) -0.19803(16) 0.4626(2) 0.0465(4) Uani 1 1 d . . . . .
C9 C -0.00546(19) -0.29016(16) 0.55114(19) 0.0322(3) Uani 1 1 d . . . . .
N10 N -0.04372(18) -0.33107(15) 0.67045(17) 0.0382(3) Uani 1 1 d . . . . .
C11 C 0.0596(2) -0.42705(17) 0.73257(18) 0.0339(4) Uani 1 1 d . . . . .
N12 N 0.0561(3) -0.49052(18) 0.8509(2) 0.0523(5) Uani 1 1 d . . . . .
N1H N 0.4399(2) -0.68836(15) 0.4791(2) 0.0412(4) Uani 1 1 d D . . . .
H11 H 0.537(4) -0.739(4) 0.483(5) 0.138(18) Uiso 1 1 d D . . . .
H12 H 0.326(3) -0.698(4) 0.413(3) 0.099(11) Uiso 1 1 d D . . . .
H13 H 0.430(6) -0.730(4) 0.560(3) 0.121(14) Uiso 1 1 d D . . . .
N2H N 0.6279(2) -0.5301(2) 0.71663(19) 0.0396(4) Uani 1 1 d . . . . .
H21 H 0.575(6) -0.527(4) 0.770(5) 0.096(13) Uiso 1 1 d . . . . .
H22 H 0.689(5) -0.476(4) 0.755(5) 0.089(13) Uiso 1 1 d . . . . .
H23 H 0.684(5) -0.586(4) 0.724(4) 0.096(13) 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
Cu N1H 2.0351(16) . ?
Cu N1H 2.0351(16) 3_646 ?
Cu N2H 2.0398(17) . ?
Cu N2H 2.0398(17) 3_646 ?
Cu N4 2.5914(13) . ?
Cu N4 2.5915(13) 3_646 ?
O1 N12 1.383(3) . ?
O1 N2 1.394(2) . ?
N2 C3 1.315(2) . ?
C3 N4 1.351(2) . ?
C3 C11 1.449(2) . ?
N4 C5 1.343(2) . ?
C5 N6 1.322(2) . ?
C5 C9 1.452(2) . ?
N6 O7 1.392(2) . ?
O7 N8 1.381(2) . ?
N8 C9 1.316(2) . ?
C9 N10 1.348(2) . ?
N10 C11 1.341(2) . ?
C11 N12 1.321(2) . ?
N1H H11 0.962(19) . ?
N1H H12 0.973(19) . ?
N1H H13 0.916(19) . ?
N2H H21 0.77(5) . ?
N2H H22 0.78(4) . ?
N2H H23 0.74(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
N1H Cu N1H 180.0 . 3_646 ?
N1H Cu N2H 89.13(8) . . ?
N1H Cu N2H 90.87(8) 3_646 . ?
N1H Cu N2H 90.87(8) . 3_646 ?
N1H Cu N2H 89.12(8) 3_646 3_646 ?
N2H Cu N2H 180.0 . 3_646 ?
N1H Cu N4 93.33(5) . . ?
N1H Cu N4 86.67(5) 3_646 . ?
N2H Cu N4 91.67(6) . . ?
N2H Cu N4 88.32(6) 3_646 . ?
N1H Cu N4 86.67(5) . 3_646 ?
N1H Cu N4 93.33(5) 3_646 3_646 ?
N2H Cu N4 88.32(6) . 3_646 ?
N2H Cu N4 91.68(6) 3_646 3_646 ?
N4 Cu N4 180.0 . 3_646 ?
N12 O1 N2 113.06(14) . . ?
C3 N2 O1 104.02(15) . . ?
N2 C3 N4 125.34(16) . . ?
N2 C3 C11 109.56(16) . . ?
N4 C3 C11 125.09(16) . . ?
C5 N4 C3 109.02(13) . . ?
C5 N4 Cu 125.10(10) . . ?
C3 N4 Cu 124.43(11) . . ?
N6 C5 N4 125.57(14) . . ?
N6 C5 C9 108.76(15) . . ?
N4 C5 C9 125.67(14) . . ?
C5 N6 O7 104.31(13) . . ?
N8 O7 N6 113.04(13) . . ?
C9 N8 O7 104.57(14) . . ?
N8 C9 N10 125.37(16) . . ?
N8 C9 C5 109.32(16) . . ?
N10 C9 C5 125.31(15) . . ?
C11 N10 C9 108.92(13) . . ?
N12 C11 N10 125.13(16) . . ?
N12 C11 C3 108.87(17) . . ?
N10 C11 C3 126.00(15) . . ?
C11 N12 O1 104.49(16) . . ?
Cu N1H H11 110(3) . . ?
Cu N1H H12 109(2) . . ?
H11 N1H H12 128(3) . . ?
Cu N1H H13 118(3) . . ?
H11 N1H H13 90(4) . . ?
H12 N1H H13 100(4) . . ?
Cu N2H H21 116(3) . . ?
Cu N2H H22 115(3) . . ?
H21 N2H H22 95(4) . . ?
Cu N2H H23 109(3) . . ?
H21 N2H H23 117(4) . . ?
H22 N2H H23 103(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
N1H H12 N10 0.973(19) 2.27(2) 3.185(2) 157(3) 3_546 yes
N2H H21 N2 0.77(5) 2.62(5) 3.244(3) 139(4) . yes
N2H H21 O7 0.77(5) 2.59(4) 3.048(2) 120(3) 4_656 yes
N2H H23 N6 0.74(5) 2.53(4) 3.193(2) 149(4) 3_646 yes

_refine_diff_density_max         0.220
_refine_diff_density_min         -0.467
_refine_diff_density_rms         0.069

####################################################################### 
# 
# 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_525s
_database_code_depnum_ccdc_archive 'CCDC 2408085'
loop_
_audit_author_name
_audit_author_address
'Galina Romanenko'
;International Tomography Center
Russia
;
_audit_update_record             
;
2024-12-05 deposited with the CCDC.	2025-10-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H12 N12 Ni O10'
_chemical_formula_weight         495.01

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'
Ni Ni 0.3393 1.1124 '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                   9.2553(5)
_cell_length_b                   6.5752(4)
_cell_length_c                   14.3428(7)
_cell_angle_alpha                90
_cell_angle_beta                 95.900(4)
_cell_angle_gamma                90
_cell_volume                     868.21(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2675
_cell_measurement_theta_min      2.51
_cell_measurement_theta_max      25.27

_exptl_crystal_description       plate
_exptl_crystal_colour            black
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.893
_exptl_crystal_F_000             504
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.03
_exptl_absorpt_coefficient_mu    1.205
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.2351
_exptl_absorpt_correction_T_max  0.2961
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(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            8447
_diffrn_reflns_av_unetI/netI     0.0685
_diffrn_reflns_av_R_equivalents  0.0791
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.427
_diffrn_reflns_theta_max         28.174
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             2138
_reflns_number_gt                1457
_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. Completness statistics refer to single and 
 composite reflections containing twin component 1 only. 
;

_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-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
; 
 Refined as a 2-component twin. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1196P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2138
_refine_ls_number_parameters     169
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0810
_refine_ls_R_factor_gt           0.0565
_refine_ls_wR_factor_ref         0.1806
_refine_ls_wR_factor_gt          0.1646
_refine_ls_goodness_of_fit_ref   0.966
_refine_ls_restrained_S_all      0.965
_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
Ni Ni 0.000000 0.000000 0.000000 0.0241(3) Uani 1 2 d S . P . .
O1 O 0.2765(4) 0.4963(4) 0.2019(2) 0.0437(8) Uani 1 1 d . . . . .
N2 N 0.1817(4) 0.3801(5) 0.1409(2) 0.0384(9) Uani 1 1 d . . . . .
C3 C 0.2599(4) 0.2188(6) 0.1222(2) 0.0264(8) Uani 1 1 d . . . . .
N4 N 0.2113(4) 0.0585(5) 0.0682(2) 0.0261(7) Uani 1 1 d . . . . .
C5 C 0.3198(4) -0.0788(6) 0.0663(2) 0.0269(8) Uani 1 1 d . . . . .
N6 N 0.3110(4) -0.2518(5) 0.0197(3) 0.0416(9) Uani 1 1 d . . . . .
O7 O 0.4454(3) -0.3415(5) 0.0404(2) 0.0506(9) Uani 1 1 d . . . . .
N8 N 0.5401(4) -0.2221(6) 0.0984(3) 0.0475(10) Uani 1 1 d . . . . .
C9 C 0.4627(4) -0.0600(7) 0.1159(3) 0.0316(9) Uani 1 1 d . . . . .
N10 N 0.5104(4) 0.0968(6) 0.1711(2) 0.0349(8) Uani 1 1 d . . . . .
C11 C 0.4023(4) 0.2354(6) 0.1716(3) 0.0294(8) Uani 1 1 d . . . . .
N12 N 0.4122(4) 0.4064(6) 0.2204(2) 0.0390(8) Uani 1 1 d . . . . .
O1W O -0.0944(3) 0.0888(5) 0.11893(18) 0.0348(7) Uani 1 1 d D . . . .
H11 H -0.126(5) 0.230(4) 0.122(3) 0.049(14) Uiso 1 1 d D . . . .
H12 H -0.053(9) 0.033(9) 0.180(3) 0.11(3) Uiso 1 1 d D . . . .
O2W O -0.0007(3) -0.2886(4) 0.0522(2) 0.0376(7) Uani 1 1 d D . . . .
H21 H -0.052(6) -0.324(11) 0.106(3) 0.10(2) Uiso 1 1 d D . . . .
H22 H 0.089(5) -0.369(11) 0.062(6) 0.14(3) Uiso 1 1 d D . . . .
O11W O 0.6881(4) 0.0213(5) 0.3415(3) 0.0500(9) Uani 1 1 d D . . . .
H111 H 0.781(4) 0.085(11) 0.361(5) 0.10(2) Uiso 1 1 d D . . . .
H112 H 0.617(17) -0.01(2) 0.387(11) 0.123 Uiso 0.5 1 d D U P . .
H113 H 0.71(2) 0.007(19) 0.275(5) 0.123 Uiso 0.5 1 d D U 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
Ni O2W 2.040(3) . ?
Ni O2W 2.040(3) 3 ?
Ni O1W 2.078(3) . ?
Ni O1W 2.078(3) 3 ?
Ni N4 2.130(3) . ?
Ni N4 2.130(3) 3 ?
O1 N12 1.388(5) . ?
O1 N2 1.400(5) . ?
N2 C3 1.326(5) . ?
C3 N4 1.357(5) . ?
C3 C11 1.436(5) . ?
N4 C5 1.352(5) . ?
C5 N6 1.317(5) . ?
C5 C9 1.442(6) . ?
N6 O7 1.381(4) . ?
O7 N8 1.388(5) . ?
N8 C9 1.323(5) . ?
C9 N10 1.346(6) . ?
N10 C11 1.353(5) . ?
C11 N12 1.323(5) . ?
O1W H11 0.97(2) . ?
O1W H12 0.99(2) . ?
O2W H21 0.98(2) . ?
O2W H22 0.98(2) . ?
O11W H111 0.97(2) . ?
O11W H112 0.99(2) . ?
O11W H113 1.00(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
O2W Ni O2W 180.0 . 3 ?
O2W Ni O1W 86.71(12) . . ?
O2W Ni O1W 93.29(12) 3 . ?
O2W Ni O1W 93.29(12) . 3 ?
O2W Ni O1W 86.71(12) 3 3 ?
O1W Ni O1W 180.00(14) . 3 ?
O2W Ni N4 92.11(12) . . ?
O2W Ni N4 87.89(12) 3 . ?
O1W Ni N4 90.92(12) . . ?
O1W Ni N4 89.08(12) 3 . ?
O2W Ni N4 87.89(12) . 3 ?
O2W Ni N4 92.11(12) 3 3 ?
O1W Ni N4 89.08(12) . 3 ?
O1W Ni N4 90.92(12) 3 3 ?
N4 Ni N4 180.0 . 3 ?
N12 O1 N2 112.5(3) . . ?
C3 N2 O1 104.1(3) . . ?
N2 C3 N4 125.5(3) . . ?
N2 C3 C11 109.4(3) . . ?
N4 C3 C11 125.0(3) . . ?
C5 N4 C3 109.1(3) . . ?
C5 N4 Ni 121.2(3) . . ?
C3 N4 Ni 129.6(2) . . ?
N6 C5 N4 125.4(4) . . ?
N6 C5 C9 109.3(3) . . ?
N4 C5 C9 125.3(4) . . ?
C5 N6 O7 104.6(3) . . ?
N6 O7 N8 112.8(3) . . ?
C9 N8 O7 104.4(3) . . ?
N8 C9 N10 125.3(4) . . ?
N8 C9 C5 108.9(4) . . ?
N10 C9 C5 125.8(4) . . ?
C9 N10 C11 108.7(3) . . ?
N12 C11 N10 124.4(4) . . ?
N12 C11 C3 109.6(3) . . ?
N10 C11 C3 126.0(3) . . ?
C11 N12 O1 104.4(3) . . ?
Ni O1W H11 117(3) . . ?
Ni O1W H12 118(5) . . ?
H11 O1W H12 114(5) . . ?
Ni O2W H21 122(4) . . ?
Ni O2W H22 121(5) . . ?
H21 O2W H22 104(6) . . ?
H111 O11W H112 122(10) . . ?
H111 O11W H113 93(10) . . ?
H112 O11W H113 145(10) . . ?

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
O1W H11 O11W 0.97(2) 2.08(2) 3.044(5) 168(4) 2 yes
O1W H12 N12 0.99(2) 2.01(3) 2.966(4) 161(7) 2_545 yes
O2W H21 O11W 0.98(2) 1.84(4) 2.728(5) 149(6) 2_545 yes
O2W H22 N2 0.98(2) 2.13(6) 2.962(4) 141(7) 1_545 yes
O2W H22 N6 0.98(2) 2.33(7) 2.979(5) 123(6) . yes
O11W H111 N8 0.97(2) 2.12(3) 3.078(5) 168(7) 2_655 yes
O11W H112 O2W 0.99(2) 2.06(12) 2.728(5) 123(10) 2 yes

_refine_diff_density_max         1.406
_refine_diff_density_min         -0.535
_refine_diff_density_rms         0.137


# start Validation Reply Form
_vrf_PLAT430_525s                
;
PROBLEM: Short Inter D...A Contact O7 ..O7 . 2.64 Ang.
RESPONSE: Specific intermolecular contact
;
# end Validation Reply Form
####################################################################### 
# 
# 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_514
_database_code_depnum_ccdc_archive 'CCDC 2408083'
loop_
_audit_author_name
_audit_author_address
'Galina Romanenko'
;International Tomography Center
Russia
;
_audit_update_record             
;
2024-12-05 deposited with the CCDC.	2025-10-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H12 N16 Ni O4'
_chemical_formula_weight         455.05

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni -3.0029 0.5091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 '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                   8.3767(3)
_cell_length_b                   11.2253(4)
_cell_length_c                   9.2089(3)
_cell_angle_alpha                90
_cell_angle_beta                 111.9995(14)
_cell_angle_gamma                90
_cell_volume                     802.87(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3681
_cell_measurement_theta_min      6.10
_cell_measurement_theta_max      67.74

_exptl_crystal_description       prism
_exptl_crystal_colour            black
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.882
_exptl_crystal_F_000             464
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.012
_exptl_crystal_size_min          0.01
_exptl_absorpt_coefficient_mu    2.359
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_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     1.54178
_diffrn_radiation_type           CuK\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            5683
_diffrn_reflns_av_unetI/netI     0.0199
_diffrn_reflns_av_R_equivalents  0.0241
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         6.099
_diffrn_reflns_theta_max         67.864
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             1437
_reflns_number_gt                1333
_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-2018/3 (Sheldrick, 2018)'
_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)+(0.0494P)²+0.3658P] 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         1437
_refine_ls_number_parameters     157
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0314
_refine_ls_R_factor_gt           0.0295
_refine_ls_wR_factor_ref         0.0842
_refine_ls_wR_factor_gt          0.0823
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_restrained_S_all      1.076
_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
Ni Ni 0.000000 0.000000 0.500000 0.02518(17) Uani 1 2 d S . P . .
O1 O 0.2382(2) 0.07353(15) 0.10392(16) 0.0452(4) Uani 1 1 d . . . . .
N2 N 0.1546(2) 0.06191(16) 0.20892(18) 0.0373(4) Uani 1 1 d . . . . .
C3 C 0.2460(2) -0.01846(15) 0.3099(2) 0.0264(4) Uani 1 1 d . . . . .
N4 N 0.21522(18) -0.05868(13) 0.43570(16) 0.0256(3) Uani 1 1 d . . . . .
C5 C 0.3347(2) -0.14108(15) 0.51270(19) 0.0254(4) Uani 1 1 d . . . . .
N6 N 0.3439(2) -0.19891(14) 0.64015(19) 0.0348(4) Uani 1 1 d . . . . .
O7 O 0.49194(18) -0.26937(13) 0.67675(17) 0.0410(4) Uani 1 1 d . . . . .
N8 N 0.5726(2) -0.25565(16) 0.5724(2) 0.0406(4) Uani 1 1 d . . . . .
C9 C 0.4773(2) -0.17740(17) 0.4694(2) 0.0301(4) Uani 1 1 d . . . . .
N10 N 0.5090(2) -0.13666(16) 0.34519(19) 0.0360(4) Uani 1 1 d . . . . .
C11 C 0.3882(2) -0.05679(17) 0.2674(2) 0.0306(4) Uani 1 1 d . . . . .
N12 N 0.3811(3) 0.00171(16) 0.1405(2) 0.0437(5) Uani 1 1 d . . . . .
N1W N 0.0612(3) 0.18140(16) 0.4793(3) 0.0376(4) Uani 1 1 d . . . . .
H12 H 0.169(8) 0.198(4) 0.511(6) 0.138(18) Uiso 1 1 d . . . . .
H13 H 0.026(10) 0.213(8) 0.546(9) 0.21(3) Uiso 1 1 d . . . . .
H11 H 0.028(6) 0.212(4) 0.396(5) 0.107(15) Uiso 1 1 d . . . . .
N2W N 0.1695(3) 0.0043(2) 0.7366(2) 0.0372(4) Uani 1 1 d . . . . .
H21 H 0.217(5) -0.051(4) 0.771(4) 0.084(13) Uiso 1 1 d . . . . .
H22 H 0.221(8) 0.056(5) 0.776(7) 0.16(2) Uiso 1 1 d . . . . .
H23 H 0.124(6) 0.000(3) 0.802(6) 0.097(15) 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
Ni N2W 2.1093(18) 3_556 ?
Ni N2W 2.1093(18) . ?
Ni N1W 2.1257(18) 3_556 ?
Ni N1W 2.1257(18) . ?
Ni N4 2.1987(14) 3_556 ?
Ni N4 2.1987(14) . ?
O1 N12 1.376(3) . ?
O1 N2 1.397(2) . ?
N2 C3 1.316(3) . ?
C3 N4 1.355(2) . ?
C3 C11 1.451(3) . ?
N4 C5 1.352(2) . ?
C5 N6 1.318(2) . ?
C5 C9 1.452(2) . ?
N6 O7 1.401(2) . ?
O7 N8 1.374(2) . ?
N8 C9 1.320(3) . ?
C9 N10 1.348(2) . ?
N10 C11 1.341(3) . ?
C11 N12 1.322(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
N2W Ni N2W 180.0 3_556 . ?
N2W Ni N1W 88.79(9) 3_556 3_556 ?
N2W Ni N1W 91.21(9) . 3_556 ?
N2W Ni N1W 91.21(9) 3_556 . ?
N2W Ni N1W 88.79(9) . . ?
N1W Ni N1W 180.0 3_556 . ?
N2W Ni N4 89.00(7) 3_556 3_556 ?
N2W Ni N4 91.00(7) . 3_556 ?
N1W Ni N4 90.76(6) 3_556 3_556 ?
N1W Ni N4 89.24(6) . 3_556 ?
N2W Ni N4 91.00(7) 3_556 . ?
N2W Ni N4 89.00(7) . . ?
N1W Ni N4 89.24(6) 3_556 . ?
N1W Ni N4 90.76(6) . . ?
N4 Ni N4 180.0 3_556 . ?
N12 O1 N2 113.06(14) . . ?
C3 N2 O1 104.05(15) . . ?
N2 C3 N4 125.84(17) . . ?
N2 C3 C11 109.42(16) . . ?
N4 C3 C11 124.73(16) . . ?
C5 N4 C3 109.61(14) . . ?
C5 N4 Ni 125.75(11) . . ?
C3 N4 Ni 124.63(11) . . ?
N6 C5 N4 126.08(16) . . ?
N6 C5 C9 109.04(16) . . ?
N4 C5 C9 124.86(16) . . ?
C5 N6 O7 104.11(14) . . ?
N8 O7 N6 113.00(13) . . ?
C9 N8 O7 104.70(14) . . ?
N8 C9 N10 125.27(16) . . ?
N8 C9 C5 109.14(16) . . ?
N10 C9 C5 125.58(17) . . ?
C11 N10 C9 109.31(15) . . ?
N12 C11 N10 125.39(18) . . ?
N12 C11 C3 108.73(17) . . ?
N10 C11 C3 125.88(16) . . ?
C11 N12 O1 104.74(16) . . ?

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
N1W H12 N8 0.86(6) 2.64(6) 3.381(2) 146(4) 3_656 yes
N1W H12 N10 0.86(6) 2.61(6) 3.386(3) 151(4) 3_656 yes
N1W H13 O7 0.85(8) 2.62(7) 3.404(2) 153(7) 2_556 yes
N2W H21 N6 0.75(4) 2.51(4) 3.017(3) 127(4) . yes
N2W H23 N2 0.83(5) 2.40(5) 3.032(3) 134(4) 3_556 yes

_refine_diff_density_max         0.414
_refine_diff_density_min         -0.324
_refine_diff_density_rms         0.054

