#------------------------------------------------------------------------------
#$Date: 2025-08-19 12:43:10 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301803 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/59/2205981.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_2205981
loop_
_publ_author_name
'Ru-Qiang Zou'
'Qiang Xu'
_publ_section_title
;
 Tris(4,4',5,5'-tetramethyl-2,2'-biimidazole)zinc(II) dinitrate
;
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m1075
_journal_page_last               m1076
_journal_paper_doi               10.1107/S1600536805013954
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          '[Zn (C10 H14 N4)3] (N O3)2'
_chemical_formula_moiety         'C30 H42 N12 Zn 2+, 2N1 O3 -'
_chemical_formula_sum            'C30 H42 N14 O6 Zn'
_chemical_formula_weight         760.15
_chemical_name_systematic
;
Tris(4,4',5,5'-tetramethyl-2,2'-biimidazole)zinc(II) dinitrate
;
_space_group_IT_number           172
_symmetry_cell_setting           hexagonal
_symmetry_space_group_name_Hall  'P 64'
_symmetry_space_group_name_H-M   'P 64'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_formula_units_Z            3
_cell_length_a                   13.900(2)
_cell_length_b                   13.900(2)
_cell_length_c                   16.809(3)
_cell_measurement_reflns_used    6512
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.105
_cell_measurement_theta_min      2.931
_cell_volume                     2812.6(8)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        'SAINT (Bruker, 1998)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 1997b)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997a)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997a)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 8.366
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1164
_diffrn_reflns_av_sigmaI/netI    0.0686
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            17035
_diffrn_reflns_theta_full        28.29
_diffrn_reflns_theta_max         28.29
_diffrn_reflns_theta_min         1.69
_diffrn_standards_interval_count 0
_diffrn_standards_number         217
_exptl_absorpt_coefficient_mu    0.715
_exptl_absorpt_correction_T_max  0.898
_exptl_absorpt_correction_T_min  0.868
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 1998)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             1194
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.679
_refine_diff_density_min         -0.305
_refine_ls_abs_structure_details 'Flack (1983), 1683 Friedel pairs'
_refine_ls_abs_structure_Flack   -0.027(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.963
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         4093
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.963
_refine_ls_R_factor_all          0.0592
_refine_ls_R_factor_gt           0.0428
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0565P)²] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1034
_refine_ls_wR_factor_ref         0.1110
_reflns_number_gt                3093
_reflns_number_total             4093
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            is6066.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'none' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_cell_volume        2812.7(8)
_cod_database_code               2205981
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z+1/3'
'-x+y, -x, z+2/3'
'-x, -y, z'
'y, -x+y, z+1/3'
'x-y, x, z+2/3'
loop_
_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_refinement_flags
_atom_site_occupancy
_atom_site_type_symbol
Zn1 0.5000 0.5000 0.17471(3) 0.05577(14) Uani d S 1 Zn
C1 0.6948(2) 0.6142(3) 0.0302(2) 0.0631(7) Uani d . 1 C
C2 0.7235(3) 0.7016(3) -0.0192(2) 0.0690(8) Uani d . 1 C
C3 0.5999(2) 0.6903(2) 0.06630(18) 0.0547(6) Uani d . 1 C
C4 0.5190(2) 0.7054(2) 0.11051(18) 0.0537(6) Uani d . 1 C
C5 0.4118(3) 0.7647(3) 0.1567(2) 0.0660(8) Uani d . 1 C
C6 0.3870(2) 0.6676(3) 0.19359(18) 0.0602(7) Uani d . 1 C
C7 0.7377(4) 0.5361(4) 0.0327(3) 0.0853(11) Uani d . 1 C
H7A 0.6786 0.4624 0.0208 0.124(18) Uiso calc R 1 H
H7B 0.7663 0.5371 0.0849 0.101(15) Uiso calc R 1 H
H7C 0.7959 0.5580 -0.0058 0.110(14) Uiso calc R 1 H
C8 0.7982(4) 0.7433(5) -0.0887(3) 0.1006(14) Uani d . 1 C
H8A 0.8315 0.6981 -0.0971 0.19(3) Uiso calc R 1 H
H8B 0.8553 0.8187 -0.0792 0.090(13) Uiso calc R 1 H
H8C 0.7564 0.7404 -0.1350 0.18(3) Uiso calc R 1 H
C9 0.3652(4) 0.8406(4) 0.1662(3) 0.0975(14) Uani d . 1 C
H9A 0.2878 0.7978 0.1795 0.097(12) Uiso calc R 1 H
H9B 0.3737 0.8797 0.1173 0.088(12) Uiso calc R 1 H
H9C 0.4043 0.8931 0.2079 0.32(6) Uiso calc R 1 H
C10 0.3023(3) 0.6062(3) 0.2551(3) 0.0779(10) Uani d . 1 C
H10A 0.2674 0.6482 0.2702 0.092(12) Uiso calc R 1 H
H10B 0.3370 0.5952 0.3008 0.13(2) Uiso calc R 1 H
H10C 0.2473 0.5355 0.2343 0.118(17) Uiso calc R 1 H
C11 0.2728(3) 0.3279(3) 0.3719(3) 0.0809(10) Uani d . 1 C
C12 0.2826(3) 0.3402(3) 0.2912(2) 0.0713(9) Uani d . 1 C
C13 0.4431(3) 0.4572(3) 0.3424(2) 0.0676(8) Uani d . 1 C
C14 0.1718(5) 0.2489(5) 0.4200(3) 0.1225(18) Uani d . 1 C
H14A 0.1899 0.2590 0.4756 0.184 Uiso calc R 1 H
H14B 0.1489 0.1738 0.4051 0.184 Uiso calc R 1 H
H14C 0.1125 0.2637 0.4097 0.184 Uiso calc R 1 H
C15 0.1956(3) 0.2814(4) 0.2278(3) 0.0860(11) Uani d . 1 C
H15A 0.1288 0.2240 0.2518 0.14(2) Uiso calc R 1 H
H15B 0.2224 0.2491 0.1896 0.096(13) Uiso calc R 1 H
H15C 0.1803 0.3337 0.2017 0.096(14) Uiso calc R 1 H
N1 0.6162(2) 0.6072(2) 0.08389(16) 0.0578(6) Uani d . 1 N
N2 0.45547(18) 0.63124(19) 0.16345(16) 0.0554(5) Uani d . 1 N
N3 0.4953(2) 0.7866(2) 0.10390(16) 0.0618(6) Uani d . 1 N
H3A 0.5266 0.8426 0.0723 0.060(9) Uiso calc R 1 H
N4 0.6626(2) 0.7494(2) 0.00532(17) 0.0624(6) Uani d . 1 N
H4A 0.6646 0.8071 -0.0151 0.072(10) Uiso calc R 1 H
N5 0.3904(2) 0.4200(2) 0.27343(17) 0.0642(6) Uani d . 1 N
N6 0.3722(3) 0.4018(3) 0.4034(2) 0.0811(9) Uani d . 1 N
H6A 0.3879 0.4121 0.4533 0.16(3) Uiso calc R 1 H
N7 0.9754(2) 0.3546(3) 0.2781(2) 0.0815(9) Uani d . 1 N
O1 0.9869(3) 0.3607(4) 0.3503(2) 0.1347(15) Uani d . 1 O
O2 1.0435(2) 0.4214(3) 0.2309(2) 0.1163(11) Uani d . 1 O
O3 0.8911(3) 0.2796(2) 0.2513(2) 0.1055(9) Uani d . 1 O
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'
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
N5 Zn1 N5 4_665 . 78.88(16)
N5 Zn1 N1 4_665 4_665 170.31(10)
N5 Zn1 N1 . 4_665 95.51(10)
N5 Zn1 N1 4_665 . 95.51(10)
N5 Zn1 N1 . . 170.31(10)
N1 Zn1 N1 4_665 . 91.09(14)
N5 Zn1 N2 4_665 . 93.33(9)
N5 Zn1 N2 . . 94.26(9)
N1 Zn1 N2 4_665 . 94.97(9)
N1 Zn1 N2 . . 78.07(9)
N5 Zn1 N2 4_665 4_665 94.26(9)
N5 Zn1 N2 . 4_665 93.33(9)
N1 Zn1 N2 4_665 4_665 78.07(9)
N1 Zn1 N2 . 4_665 94.97(9)
N2 Zn1 N2 . 4_665 170.17(14)
C2 C1 N1 . . 109.3(3)
C2 C1 C7 . . 129.1(3)
N1 C1 C7 . . 121.6(3)
C1 C2 N4 . . 105.9(3)
C1 C2 C8 . . 132.1(3)
N4 C2 C8 . . 122.0(3)
N1 C3 N4 . . 111.6(3)
N1 C3 C4 . . 119.9(3)
N4 C3 C4 . . 128.5(3)
N2 C4 N3 . . 111.6(3)
N2 C4 C3 . . 120.0(2)
N3 C4 C3 . . 128.3(3)
C6 C5 N3 . . 106.3(2)
C6 C5 C9 . . 131.7(3)
N3 C5 C9 . . 122.0(3)
C5 C6 N2 . . 108.5(3)
C5 C6 C10 . . 128.6(3)
N2 C6 C10 . . 122.9(3)
C1 C7 H7A . . 109.5
C1 C7 H7B . . 109.5
H7A C7 H7B . . 109.5
C1 C7 H7C . . 109.5
H7A C7 H7C . . 109.5
H7B C7 H7C . . 109.5
C2 C8 H8A . . 109.5
C2 C8 H8B . . 109.5
H8A C8 H8B . . 109.5
C2 C8 H8C . . 109.5
H8A C8 H8C . . 109.5
H8B C8 H8C . . 109.5
C5 C9 H9A . . 109.5
C5 C9 H9B . . 109.5
H9A C9 H9B . . 109.5
C5 C9 H9C . . 109.5
H9A C9 H9C . . 109.5
H9B C9 H9C . . 109.5
C6 C10 H10A . . 109.5
C6 C10 H10B . . 109.5
H10A C10 H10B . . 109.5
C6 C10 H10C . . 109.5
H10A C10 H10C . . 109.5
H10B C10 H10C . . 109.5
N6 C11 C12 . . 107.1(4)
N6 C11 C14 . . 124.6(4)
C12 C11 C14 . . 128.3(5)
C11 C12 N5 . . 108.5(4)
C11 C12 C15 . . 129.1(4)
N5 C12 C15 . . 122.4(3)
N5 C13 N6 . . 109.5(3)
N5 C13 C13 . 4_665 119.3(2)
N6 C13 C13 . 4_665 131.2(2)
C11 C14 H14A . . 109.5
C11 C14 H14B . . 109.5
H14A C14 H14B . . 109.5
C11 C14 H14C . . 109.5
H14A C14 H14C . . 109.5
H14B C14 H14C . . 109.5
C12 C15 H15A . . 109.5
C12 C15 H15B . . 109.5
H15A C15 H15B . . 109.5
C12 C15 H15C . . 109.5
H15A C15 H15C . . 109.5
H15B C15 H15C . . 109.5
C3 N1 C1 . . 105.5(3)
C3 N1 Zn1 . . 111.30(19)
C1 N1 Zn1 . . 142.6(2)
C4 N2 C6 . . 106.1(2)
C4 N2 Zn1 . . 110.51(18)
C6 N2 Zn1 . . 143.3(2)
C4 N3 C5 . . 107.4(3)
C4 N3 H3A . . 126.3
C5 N3 H3A . . 126.3
C3 N4 C2 . . 107.7(3)
C3 N4 H4A . . 126.1
C2 N4 H4A . . 126.1
C13 N5 C12 . . 106.8(3)
C13 N5 Zn1 . . 111.2(2)
C12 N5 Zn1 . . 142.0(3)
C11 N6 C13 . . 108.1(4)
C11 N6 H6A . . 125.9
C13 N6 H6A . . 125.9
O3 N7 O1 . . 118.0(4)
O3 N7 O2 . . 117.5(4)
O1 N7 O2 . . 124.4(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
Zn1 N5 4_665 2.149(3)
Zn1 N5 . 2.149(3)
Zn1 N1 4_665 2.180(3)
Zn1 N1 . 2.180(3)
Zn1 N2 . 2.208(2)
Zn1 N2 4_665 2.208(2)
C1 C2 . 1.356(5)
C1 N1 . 1.383(4)
C1 C7 . 1.477(5)
C2 N4 . 1.375(4)
C2 C8 . 1.476(6)
C3 N1 . 1.318(4)
C3 N4 . 1.330(4)
C3 C4 . 1.448(4)
C4 N2 . 1.313(4)
C4 N3 . 1.329(4)
C5 C6 . 1.364(5)
C5 N3 . 1.370(4)
C5 C9 . 1.497(5)
C6 N2 . 1.378(4)
C6 C10 . 1.476(5)
C7 H7A . 0.9600
C7 H7B . 0.9600
C7 H7C . 0.9600
C8 H8A . 0.9600
C8 H8B . 0.9600
C8 H8C . 0.9600
C9 H9A . 0.9600
C9 H9B . 0.9600
C9 H9C . 0.9600
C10 H10A . 0.9600
C10 H10B . 0.9600
C10 H10C . 0.9600
C11 N6 . 1.351(6)
C11 C12 . 1.365(6)
C11 C14 . 1.512(6)
C12 N5 . 1.380(5)
C12 C15 . 1.509(6)
C13 N5 . 1.331(5)
C13 N6 . 1.363(5)
C13 C13 4_665 1.426(7)
C14 H14A . 0.9600
C14 H14B . 0.9600
C14 H14C . 0.9600
C15 H15A . 0.9600
C15 H15B . 0.9600
C15 H15C . 0.9600
N3 H3A . 0.8600
N4 H4A . 0.8600
N6 H6A . 0.8600
N7 O3 . 1.202(4)
N7 O1 . 1.221(5)
N7 O2 . 1.228(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
N3 H3A O1 6_554 0.86 2.01 2.852(4) 167
N4 H4A O3 6_554 0.86 2.01 2.818(5) 156
N6 H6A O2 5_565 0.86 2.03 2.849(5) 157
N6 H6A O3 5_565 0.86 2.60 3.276(5) 136
C9 H9A O3 4_665 0.96 2.47 3.403(7) 163
C9 H9B O1 3_674 0.96 2.51 3.431(7) 162
C10 H10C O2 1_455 0.96 2.46 3.235(6) 138
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
N1 C1 C2 N4 . 0.7(4)
C7 C1 C2 N4 . -177.6(4)
N1 C1 C2 C8 . -176.6(4)
C7 C1 C2 C8 . 5.1(7)
N1 C3 C4 N2 . -5.6(4)
N4 C3 C4 N2 . 172.3(3)
N1 C3 C4 N3 . 176.5(3)
N4 C3 C4 N3 . -5.6(5)
N3 C5 C6 N2 . 0.3(3)
C9 C5 C6 N2 . -179.4(4)
N3 C5 C6 C10 . -179.3(3)
C9 C5 C6 C10 . 1.1(7)
N6 C11 C12 N5 . 2.1(4)
C14 C11 C12 N5 . -178.6(4)
N6 C11 C12 C15 . -177.6(3)
C14 C11 C12 C15 . 1.8(7)
N4 C3 N1 C1 . 0.0(3)
C4 C3 N1 C1 . 178.3(3)
N4 C3 N1 Zn1 . -173.5(2)
C4 C3 N1 Zn1 . 4.7(3)
C2 C1 N1 C3 . -0.5(4)
C7 C1 N1 C3 . 178.0(3)
C2 C1 N1 Zn1 . 169.6(3)
C7 C1 N1 Zn1 . -11.9(6)
N5 Zn1 N1 C3 4_665 -94.5(2)
N1 Zn1 N1 C3 4_665 92.6(2)
N2 Zn1 N1 C3 . -2.3(2)
N2 Zn1 N1 C3 4_665 170.7(2)
N5 Zn1 N1 C1 4_665 95.8(4)
N1 Zn1 N1 C1 4_665 -77.1(3)
N2 Zn1 N1 C1 . -172.0(4)
N2 Zn1 N1 C1 4_665 1.0(4)
N3 C4 N2 C6 . -0.6(3)
C3 C4 N2 C6 . -178.8(3)
N3 C4 N2 Zn1 . -178.7(2)
C3 C4 N2 Zn1 . 3.1(3)
C5 C6 N2 C4 . 0.2(3)
C10 C6 N2 C4 . 179.8(3)
C5 C6 N2 Zn1 . 177.1(3)
C10 C6 N2 Zn1 . -3.3(5)
N5 Zn1 N2 C4 4_665 94.5(2)
N5 Zn1 N2 C4 . 173.5(2)
N1 Zn1 N2 C4 4_665 -90.6(2)
N1 Zn1 N2 C4 . -0.48(19)
N5 Zn1 N2 C6 4_665 -82.4(3)
N5 Zn1 N2 C6 . -3.3(3)
N1 Zn1 N2 C6 4_665 92.6(3)
N1 Zn1 N2 C6 . -177.3(3)
N2 C4 N3 C5 . 0.8(3)
C3 C4 N3 C5 . 178.8(3)
C6 C5 N3 C4 . -0.6(3)
C9 C5 N3 C4 . 179.0(4)
N1 C3 N4 C2 . 0.4(3)
C4 C3 N4 C2 . -177.6(3)
C1 C2 N4 C3 . -0.7(4)
C8 C2 N4 C3 . 177.0(4)
N6 C13 N5 C12 . 1.0(3)
C13 C13 N5 C12 4_665 -178.9(3)
N6 C13 N5 Zn1 . -177.79(18)
C13 C13 N5 Zn1 4_665 2.4(4)
C11 C12 N5 C13 . -1.9(4)
C15 C12 N5 C13 . 177.8(3)
C11 C12 N5 Zn1 . 176.3(3)
C15 C12 N5 Zn1 . -4.1(5)
N5 Zn1 N5 C13 4_665 -0.8(3)
N1 Zn1 N5 C13 4_665 171.2(2)
N2 Zn1 N5 C13 . -93.4(2)
N2 Zn1 N5 C13 4_665 92.9(2)
N5 Zn1 N5 C12 4_665 -178.9(4)
N1 Zn1 N5 C12 4_665 -6.9(3)
N2 Zn1 N5 C12 . 88.5(3)
N2 Zn1 N5 C12 4_665 -85.2(3)
C12 C11 N6 C13 . -1.4(4)
C14 C11 N6 C13 . 179.2(4)
N5 C13 N6 C11 . 0.3(3)
C13 C13 N6 C11 4_665 -179.9(4)
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1 PubChem 139067880
