#------------------------------------------------------------------------------
#$Date: 2024-12-07 19:10:59 +0200 (Sat, 07 Dec 2024) $
#$Revision: 296778 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/32/2023283.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2023283
loop_
_publ_author_name
'Reibenspies, Joseph'
'Small, Nadia'
'Bhuvanesh, Nattamai'
'Chiarella, Gina'
'Salazar, Vivian'
'Pery, Bréayshia'
'Smith, Rukiyah'
'Toole, Deja'
'Hewage, Shamika'
'Fernando, Harschica'
'Reinheimer, Eric'
_publ_section_title
;
 Crystal structure and Hirshfeld surface analysis of (nitrato-κ2
 O,O′)(1,4,7,10-tetraazacyclododecane-κ4 N)nickel(II) nitrate
;
_journal_coeditor_code           PK2709
_journal_issue                   11
_journal_name_full
'Acta Crystallographica Section E Crystallographic Communications'
_journal_page_first              1157
_journal_page_last               1160
_journal_paper_doi               10.1107/S2056989024009496
_journal_volume                  80
_journal_year                    2024
_chemical_formula_iupac          '[Ni (C8 H20 N4) (N1 O3)] N O3'
_chemical_formula_moiety         'C8 H20 N5 Ni O3 +, N O3 -'
_chemical_formula_sum            'C8 H20 N6 Ni O6'
_chemical_formula_weight         355.01
_chemical_name_systematic
'(Nitrato-κ²O,O')(1,4,7,10-tetraazacyclododecane-κ⁴N)nickel(II) nitrate'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_method
;
HOleoux2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_cell_angle_alpha                90
_cell_angle_beta                 94.973(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.7321(5)
_cell_length_b                   15.2444(9)
_cell_length_c                   10.8545(6)
_cell_measurement_reflns_used    4001
_cell_measurement_temperature    293
_cell_measurement_theta_max      29.8940
_cell_measurement_theta_min      2.2880
_cell_volume                     1439.46(14)
_computing_cell_refinement
;
CrysAlisPro 1.171.43.121a (Rigaku OD, 2024)
;
_computing_data_collection
;
CrysAlisPro 1.171.43.121a (Rigaku OD, 2024)
;
_computing_data_reduction
;
CrysAlisPro 1.171.43.121a (Rigaku OD, 2024)
;
_computing_molecular_graphics
;
Olex2 1.5 (Dolomanov et al.,  2009)
;
_computing_publication_material
;
Olex2 1.5 (Dolomanov et al.,  2009)
;
_computing_structure_refinement
;
SHELXL2019/2 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT  (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      293
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini II'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0376
_diffrn_reflns_av_unetI/netI     0.0504
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            12195
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         2.309
_exptl_absorpt_coefficient_mu    1.386
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89877
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlisPro; Rigaku OD, 2024)
;
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.638
_exptl_crystal_description       plate
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.385
_refine_diff_density_min         -0.279
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         12195
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.086
_refine_ls_R_factor_all          0.0534
_refine_ls_R_factor_gt           0.0362
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0406P)²+0.8788P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0903
_refine_ls_wR_factor_ref         0.1044
_reflns_number_gt                9604
_reflns_number_total             12195
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            pk2709.cif
_cod_data_source_block           I
_cod_depositor_comments          'Adding full bibliography for 2023283.cif.'
_cod_original_cell_volume        1439.47(14)
_cod_database_code               2023283
_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'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni Ni1 0.47429(5) 0.40178(3) 0.71868(4) 0.02627(16) Uani d 1 . .
O O1 0.6641(3) 0.44290(18) 0.8450(2) 0.0402(7) Uani d 1 . .
O O2 0.8551(3) 0.5139(2) 0.7739(3) 0.0626(10) Uani d 1 . .
O O3 0.6572(3) 0.47217(18) 0.6500(2) 0.0414(8) Uani d 1 . .
N N1 0.7303(4) 0.4775(2) 0.7575(3) 0.0395(9) Uani d 1 . .
N N2 0.3234(4) 0.5046(2) 0.7480(3) 0.0323(8) Uani d 1 . .
H H2 0.381537 0.558870 0.764991 0.039 Uiso calc 1 . .
N N5 0.3440(3) 0.38312(19) 0.5547(3) 0.0292(8) Uani d 1 . .
H H5 0.392730 0.413234 0.488510 0.035 Uiso calc 1 . .
N N8 0.5615(3) 0.2762(2) 0.6909(3) 0.0313(8) Uani d 1 . .
H H8 0.674094 0.277112 0.700910 0.038 Uiso calc 1 . .
N N11 0.3508(3) 0.3385(2) 0.8461(3) 0.0298(8) Uani d 1 . .
H H11 0.255201 0.314213 0.805949 0.036 Uiso calc 1 . .
C C1 0.2362(5) 0.4818(3) 0.8563(4) 0.0418(11) Uani d 1 . .
H H1A 0.133206 0.462931 0.827328 0.050 Uiso calc 1 . .
H H1B 0.227560 0.533312 0.907739 0.050 Uiso calc 1 . .
C C3 0.2243(5) 0.5135(3) 0.6305(4) 0.0396(11) Uani d 1 . .
H H3A 0.274368 0.551436 0.574398 0.048 Uiso calc 1 . .
H H3B 0.127546 0.540508 0.646862 0.048 Uiso calc 1 . .
C C4 0.1937(4) 0.4249(3) 0.5703(4) 0.0362(10) Uani d 1 . .
H H4A 0.134359 0.388525 0.621993 0.043 Uiso calc 1 . .
H H4B 0.135815 0.431978 0.490575 0.043 Uiso calc 1 . .
C C6 0.3441(4) 0.2873(3) 0.5311(3) 0.0344(10) Uani d 1 . .
H H6A 0.310735 0.275553 0.445087 0.041 Uiso calc 1 . .
H H6B 0.274129 0.258079 0.582361 0.041 Uiso calc 1 . .
C C7 0.5067(5) 0.2534(3) 0.5614(4) 0.0386(11) Uani d 1 . .
H H7A 0.508492 0.190241 0.550862 0.046 Uiso calc 1 . .
H H7B 0.574574 0.279217 0.505188 0.046 Uiso calc 1 . .
C C9 0.5013(5) 0.2164(3) 0.7832(4) 0.0379(11) Uani d 1 . .
H H9A 0.579747 0.173954 0.810634 0.045 Uiso calc 1 . .
H H9B 0.413183 0.184602 0.745263 0.045 Uiso calc 1 . .
C C10 0.4544(5) 0.2678(3) 0.8934(4) 0.0399(11) Uani d 1 . .
H H10A 0.402253 0.229681 0.947894 0.048 Uiso calc 1 . .
H H10B 0.544393 0.292262 0.939630 0.048 Uiso calc 1 . .
C C12 0.3177(5) 0.4090(3) 0.9320(3) 0.0382(10) Uani d 1 . .
H H12A 0.412467 0.430823 0.974336 0.046 Uiso calc 1 . .
H H12B 0.252712 0.387293 0.993362 0.046 Uiso calc 1 . .
O O4 0.1146(4) 0.2042(2) 0.7487(3) 0.0663(10) Uani d 1 . .
O O5 -0.0669(4) 0.2984(2) 0.7302(4) 0.0846(13) Uani d 1 . .
O O6 -0.1194(4) 0.1630(2) 0.7286(4) 0.0803(12) Uani d 1 . .
N N3 -0.0252(4) 0.2221(3) 0.7343(3) 0.0398(9) Uani d 1 . .
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'
Ni Ni 0.3393 1.1124 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O3 Ni1 O1 . . 60.82(10) ?
N2 Ni1 O1 . . 98.38(11) ?
N2 Ni1 O3 . . 100.29(12) ?
N2 Ni1 N8 . . 161.91(12) ?
N5 Ni1 O1 . . 159.07(12) ?
N5 Ni1 O3 . . 98.27(11) ?
N5 Ni1 N2 . . 85.77(12) ?
N5 Ni1 N8 . . 85.96(12) ?
N5 Ni1 N11 . . 103.55(12) ?
N8 Ni1 O1 . . 95.08(11) ?
N8 Ni1 O3 . . 96.80(11) ?
N11 Ni1 O1 . . 97.33(12) ?
N11 Ni1 O3 . . 158.13(11) ?
N11 Ni1 N2 . . 82.85(12) ?
N11 Ni1 N8 . . 83.49(12) ?
N1 O1 Ni1 . . 91.2(2) ?
N1 O3 Ni1 . . 92.5(2) ?
O1 N1 O3 . . 115.5(3) ?
O2 N1 O1 . . 122.6(4) ?
O2 N1 O3 . . 121.9(4) ?
Ni1 N2 H2 . . 109.8 ?
C1 N2 Ni1 . . 108.4(2) ?
C1 N2 H2 . . 109.8 ?
C3 N2 Ni1 . . 105.5(2) ?
C3 N2 H2 . . 109.8 ?
C3 N2 C1 . . 113.5(3) ?
Ni1 N5 H5 . . 109.1 ?
C4 N5 Ni1 . . 105.7(2) ?
C4 N5 H5 . . 109.1 ?
C4 N5 C6 . . 117.2(3) ?
C6 N5 Ni1 . . 106.2(2) ?
C6 N5 H5 . . 109.1 ?
Ni1 N8 H8 . . 110.2 ?
C7 N8 Ni1 . . 105.0(2) ?
C7 N8 H8 . . 110.2 ?
C9 N8 Ni1 . . 108.1(2) ?
C9 N8 H8 . . 110.2 ?
C9 N8 C7 . . 113.0(3) ?
Ni1 N11 H11 . . 110.6 ?
C10 N11 Ni1 . . 103.6(2) ?
C10 N11 H11 . . 110.6 ?
C12 N11 Ni1 . . 103.1(2) ?
C12 N11 H11 . . 110.6 ?
C12 N11 C10 . . 117.6(3) ?
N2 C1 H1A . . 109.6 ?
N2 C1 H1B . . 109.6 ?
N2 C1 C12 . . 110.3(3) ?
H1A C1 H1B . . 108.1 ?
C12 C1 H1A . . 109.6 ?
C12 C1 H1B . . 109.6 ?
N2 C3 H3A . . 109.5 ?
N2 C3 H3B . . 109.5 ?
N2 C3 C4 . . 110.9(3) ?
H3A C3 H3B . . 108.1 ?
C4 C3 H3A . . 109.5 ?
C4 C3 H3B . . 109.5 ?
N5 C4 C3 . . 107.9(3) ?
N5 C4 H4A . . 110.1 ?
N5 C4 H4B . . 110.1 ?
C3 C4 H4A . . 110.1 ?
C3 C4 H4B . . 110.1 ?
H4A C4 H4B . . 108.4 ?
N5 C6 H6A . . 110.1 ?
N5 C6 H6B . . 110.1 ?
N5 C6 C7 . . 108.2(3) ?
H6A C6 H6B . . 108.4 ?
C7 C6 H6A . . 110.1 ?
C7 C6 H6B . . 110.1 ?
N8 C7 C6 . . 110.1(3) ?
N8 C7 H7A . . 109.6 ?
N8 C7 H7B . . 109.6 ?
C6 C7 H7A . . 109.6 ?
C6 C7 H7B . . 109.6 ?
H7A C7 H7B . . 108.2 ?
N8 C9 H9A . . 109.5 ?
N8 C9 H9B . . 109.5 ?
N8 C9 C10 . . 110.5(3) ?
H9A C9 H9B . . 108.1 ?
C10 C9 H9A . . 109.5 ?
C10 C9 H9B . . 109.5 ?
N11 C10 C9 . . 107.7(3) ?
N11 C10 H10A . . 110.2 ?
N11 C10 H10B . . 110.2 ?
C9 C10 H10A . . 110.2 ?
C9 C10 H10B . . 110.2 ?
H10A C10 H10B . . 108.5 ?
N11 C12 C1 . . 107.5(3) ?
N11 C12 H12A . . 110.2 ?
N11 C12 H12B . . 110.2 ?
C1 C12 H12A . . 110.2 ?
C1 C12 H12B . . 110.2 ?
H12A C12 H12B . . 108.5 ?
O5 N3 O4 . . 120.0(4) ?
O5 N3 O6 . . 120.4(4) ?
O6 N3 O4 . . 119.6(4) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Ni1 O1 . 2.151(3) ?
Ni1 O3 . 2.113(3) ?
Ni1 N2 . 2.090(3) ?
Ni1 N5 . 2.048(3) ?
Ni1 N8 . 2.092(3) ?
Ni1 N11 . 2.065(3) ?
O1 N1 . 1.269(4) ?
O2 N1 . 1.221(4) ?
O3 N1 . 1.283(4) ?
N2 H2 . 0.9800 ?
N2 C1 . 1.496(5) ?
N2 C3 . 1.484(4) ?
N5 H5 . 0.9800 ?
N5 C4 . 1.481(4) ?
N5 C6 . 1.483(4) ?
N8 H8 . 0.9800 ?
N8 C7 . 1.487(4) ?
N8 C9 . 1.484(4) ?
N11 H11 . 0.9800 ?
N11 C10 . 1.471(4) ?
N11 C12 . 1.467(4) ?
C1 H1A . 0.9700 ?
C1 H1B . 0.9700 ?
C1 C12 . 1.521(5) ?
C3 H3A . 0.9700 ?
C3 H3B . 0.9700 ?
C3 C4 . 1.515(5) ?
C4 H4A . 0.9700 ?
C4 H4B . 0.9700 ?
C6 H6A . 0.9700 ?
C6 H6B . 0.9700 ?
C6 C7 . 1.520(5) ?
C7 H7A . 0.9700 ?
C7 H7B . 0.9700 ?
C9 H9A . 0.9700 ?
C9 H9B . 0.9700 ?
C9 C10 . 1.516(5) ?
C10 H10A . 0.9700 ?
C10 H10B . 0.9700 ?
C12 H12A . 0.9700 ?
C12 H12B . 0.9700 ?
O4 N3 . 1.248(4) ?
O5 N3 . 1.218(4) ?
O6 N3 . 1.218(4) ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N2 H2 O4 2_556 0.98 2.22 3.091(5) 147.2 yes
N5 H5 O3 3_666 0.98 2.32 3.130(4) 139.3 yes
N8 H8 O5 1_655 0.98 2.28 3.253(5) 172.4 yes
N8 H8 O6 1_655 0.98 2.50 3.273(5) 135.1 yes
N11 H11 O4 . 0.98 2.14 3.030(5) 150.6 yes
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
Ni1 O1 N1 O2 . . . . -179.3(3) ?
Ni1 O1 N1 O3 . . . . 1.0(3) ?
Ni1 O3 N1 O1 . . . . -1.0(3) ?
Ni1 O3 N1 O2 . . . . 179.3(3) ?
Ni1 N2 C1 C12 . . . . 17.8(4) ?
Ni1 N2 C3 C4 . . . . 34.8(4) ?
Ni1 N5 C4 C3 . . . . 45.1(3) ?
Ni1 N5 C6 C7 . . . . -43.1(3) ?
Ni1 N8 C7 C6 . . . . -38.1(4) ?
Ni1 N8 C9 C10 . . . . -22.5(4) ?
Ni1 N11 C10 C9 . . . . -53.5(3) ?
Ni1 N11 C12 C1 . . . . 55.7(3) ?
N2 C1 C12 N11 . . . . -50.0(4) ?
N2 C3 C4 N5 . . . . -55.3(4) ?
N5 C6 C7 N8 . . . . 56.3(4) ?
N8 C9 C10 N11 . . . . 52.0(4) ?
C1 N2 C3 C4 . . . . -83.8(4) ?
C3 N2 C1 C12 . . . . 134.6(3) ?
C4 N5 C6 C7 . . . . -160.9(3) ?
C6 N5 C4 C3 . . . . 163.1(3) ?
C7 N8 C9 C10 . . . . -138.3(3) ?
C9 N8 C7 C6 . . . . 79.5(4) ?
C10 N11 C12 C1 . . . . 168.9(3) ?
C12 N11 C10 C9 . . . . -166.4(3) ?
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.823(3)
2 0.177(3)
