#------------------------------------------------------------------------------
#$Date: 2025-08-21 01:01:10 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301838 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/32/18/4321843.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4321843
loop_
_publ_author_name
'Naohide Matsumoto'
'Yuri Motoda'
'Toshihiro Matsuo'
'Toshio Nakashima'
'Nazzareno Re'
'Francoise Dahan'
'Jean-Pierre Tuchagues'
_publ_contact_author             'Naohide Matsumoto'
_publ_contact_author_email       'naohide@aster.sci.kumamoto-u.ac.jp '
_publ_contact_author_fax         ' +81-96-342-3390 '
_publ_contact_author_phone       '+81-96-342-3390 '
_publ_section_title
;
 pH-Dependent Monomer ←→ Oligomer Interconversion of
 Copper(II) Complexes with
 N-(2-R-imidazol-4-ylmethylidene)-2-aminoethylpyridine (R = Methyl,
 Phenyl)
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              1165
_journal_page_last               1173
_journal_paper_doi               10.1021/ic981158b
_journal_volume                  38
_journal_year                    1999
_chemical_formula_sum            'C17 H15 Cu F6 N4 P'
_chemical_formula_weight         483.84
_space_group_IT_number           148
_symmetry_cell_setting           rhombohedral
_symmetry_space_group_name_Hall  '-R 3'
_symmetry_space_group_name_H-M   'R -3 :H'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_formula_units_Z            18
_cell_length_a                   29.812(5)
_cell_length_b                   29.812(5)
_cell_length_c                   11.484(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      15.3
_cell_measurement_theta_min      11.8
_cell_volume                     8839(3)
_computing_cell_refinement       CAD4-EXPRESS
_computing_data_collection       CAD4-EXPRESS
_computing_data_reduction        'MolEN (Fair, 1990)'
_computing_molecular_graphics    'ZORTEP (Zsolnai, 1996)'
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device       'Enraf-Nonius CAD4'
_diffrn_measurement_method       ω-2θ
_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  0.0268
_diffrn_reflns_av_sigmaI/netI    0.0331
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7375
_diffrn_reflns_theta_max         22.03
_diffrn_reflns_theta_min         1.94
_diffrn_standards_decay_%        0.1
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    1.259
_exptl_absorpt_correction_T_max  0.9955
_exptl_absorpt_correction_T_min  0.8336
_exptl_absorpt_correction_type   Psi-scans
_exptl_crystal_colour            Dark-grey
_exptl_crystal_density_diffrn    1.636
_exptl_crystal_description       Plate
_exptl_crystal_F_000             4374
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.042
_refine_diff_density_min         -0.051
_refine_diff_density_rms         0.035
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.064
_refine_ls_goodness_of_fit_obs   1.095
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         2409
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_restrained_S_obs      1.095
_refine_ls_R_factor_all          0.0436
_refine_ls_R_factor_obs          0.0363
_refine_ls_shift/esd_max         0.005
_refine_ls_shift/esd_mean        0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0246P)²+2.4891P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0672
_refine_ls_wR_factor_obs         0.0624
_reflns_number_observed          2047
_reflns_number_total             2409
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            ic981158b_5.cif
_cod_data_source_block           (2'b)
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Rhombohedral' changed to
'rhombohedral' according to the built-in table from CIF Core
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1673 2011-04-08 12:14:43Z adriana 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0246P)^2^+2.4891P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.0246P)^2^+2.4891P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        8839.1(31)
_cod_original_sg_symbol_H-M      'R -3'
_cod_database_code               4321843
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'
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_thermal_displace_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_group
Cu Cu 0.45176(2) 0.22739(2) 0.43582(5) 0.0458(2) Uani 1 d . .
N1 N 0.53130(12) 0.14862(12) 0.3474(3) 0.0502(9) Uani 1 d . .
N2 N 0.48989(12) 0.18991(12) 0.3951(3) 0.0469(9) Uani 1 d . .
N3 N 0.44291(12) 0.19054(12) 0.5830(3) 0.0510(9) Uani 1 d . .
N4 N 0.40253(10) 0.25090(12) 0.4833(3) 0.0479(9) Uani 1 d . .
C1 C 0.5142(2) 0.1813(2) 0.3108(4) 0.0541(11) Uani 1 d . .
C2 C 0.51546(14) 0.13687(14) 0.4558(4) 0.0456(11) Uani 1 d . .
H2 H 0.52080(14) 0.11471(14) 0.5034(4) 0.050 Uiso 1 calc R .
C3 C 0.4905(2) 0.1618(2) 0.4870(4) 0.0561(12) Uani 1 d . .
C4 C 0.4640(2) 0.1606(2) 0.5879(4) 0.0551(12) Uani 1 d . .
H4 H 0.4615(2) 0.1407(2) 0.6526(4) 0.061 Uiso 1 calc R .
C5 C 0.4164(2) 0.19573(15) 0.6871(4) 0.0568(12) Uani 1 d . .
H5A H 0.4304(2) 0.18906(15) 0.7570(4) 0.063 Uiso 1 calc R .
H5B H 0.3797(2) 0.17064(15) 0.6835(4) 0.063 Uiso 1 calc R .
C6 C 0.4244(2) 0.25028(15) 0.6912(4) 0.0552(11) Uani 1 d . .
H6A H 0.4610(2) 0.27533(15) 0.6835(4) 0.061 Uiso 1 calc R .
H6B H 0.4127(2) 0.25595(15) 0.7656(4) 0.061 Uiso 1 calc R .
C7 C 0.39434(14) 0.2579(2) 0.5928(4) 0.0532(12) Uani 1 d . .
C8 C 0.35877(14) 0.27358(14) 0.6226(3) 0.0527(11) Uani 1 d . .
H8 H 0.35418(14) 0.27966(14) 0.7000(3) 0.058 Uiso 1 calc R .
C9 C 0.33056(13) 0.27989(15) 0.5351(3) 0.0586(12) Uani 1 d . .
H9 H 0.30793(13) 0.29201(15) 0.5515(3) 0.064 Uiso 1 calc R .
C10 C 0.33694(13) 0.26767(15) 0.4221(3) 0.0580(12) Uani 1 d . .
H10 H 0.31672(13) 0.26883(15) 0.3618(3) 0.064 Uiso 1 calc R .
C11 C 0.37368(13) 0.25382(15) 0.4011(3) 0.0602(13) Uani 1 d . .
H11 H 0.37830(13) 0.24617(15) 0.3251(3) 0.066 Uiso 1 calc R .
C12 C 0.5231(2) 0.2021(2) 0.1903(4) 0.0503(11) Uani 1 d . .
C13 C 0.4810(2) 0.19267(15) 0.1213(4) 0.0448(10) Uani 1 d . .
H13 H 0.4477(2) 0.17406(15) 0.1515(4) 0.049 Uiso 1 calc R .
C14 C 0.4884(2) 0.2107(2) 0.0081(4) 0.0610(13) Uani 1 d . .
H14 H 0.4599(2) 0.2043(2) -0.0370(4) 0.067 Uiso 1 calc R .
C15 C 0.5377(2) 0.2383(2) -0.0391(4) 0.0599(12) Uani 1 d . .
H15 H 0.5424(2) 0.2504(2) -0.1152(4) 0.066 Uiso 1 calc R .
C16 C 0.5802(2) 0.2475(2) 0.0293(4) 0.0600(12) Uani 1 d . .
H16 H 0.6134(2) 0.2656(2) -0.0019(4) 0.066 Uiso 1 calc R .
C17 C 0.5733(2) 0.22977(14) 0.1445(4) 0.0524(12) Uani 1 d . .
H17 H 0.6017(2) 0.23628(14) 0.1901(4) 0.058 Uiso 1 calc R .
P P 0.77838(5) 0.67083(4) 0.33761(12) 0.0598(4) Uani 1 d . .
F1 F 0.77913(10) 0.61996(8) 0.3103(3) 0.0974(11) Uani 1 d . .
F2 F 0.83313(9) 0.70213(12) 0.2840(3) 0.1162(12) Uani 1 d . .
F3 F 0.80138(12) 0.67018(10) 0.4587(2) 0.0943(10) Uani 1 d . .
F4 F 0.77951(13) 0.72199(9) 0.3709(3) 0.1159(13) Uani 1 d . .
F5 F 0.75646(14) 0.67149(13) 0.2164(2) 0.1168(12) Uani 1 d . .
F6 F 0.72335(9) 0.63860(11) 0.3902(3) 0.1112(12) Uani 1 d . .
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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N3 Cu N1 159.34(14) . 17 ?
N3 Cu N4 92.57(14) . . ?
N1 Cu N4 89.21(13) 17 . ?
N3 Cu N2 81.03(14) . . ?
N1 Cu N2 100.01(14) 17 . ?
N4 Cu N2 168.86(13) . . ?
C2 N1 C1 105.5(3) . . ?
C2 N1 Cu 133.6(3) . 18_545 ?
C1 N1 Cu 119.2(3) . 18_545 ?
C1 N2 C3 106.0(3) . . ?
C1 N2 Cu 143.6(3) . . ?
C3 N2 Cu 110.4(3) . . ?
C4 N3 C5 119.5(4) . . ?
C4 N3 Cu 116.0(3) . . ?
C5 N3 Cu 124.5(3) . . ?
C7 N4 C11 119.8(3) . . ?
C7 N4 Cu 123.0(3) . . ?
C11 N4 Cu 116.8(3) . . ?
N2 C1 N1 110.6(4) . . ?
N2 C1 C12 127.4(4) . . ?
N1 C1 C12 122.0(4) . . ?
N1 C2 C3 109.3(4) . . ?
C2 C3 N2 108.6(4) . . ?
C2 C3 C4 132.3(5) . . ?
N2 C3 C4 119.0(4) . . ?
N3 C4 C3 113.6(4) . . ?
N3 C5 C6 109.2(4) . . ?
C5 C6 C7 110.2(4) . . ?
N4 C7 C8 121.2(3) . . ?
N4 C7 C6 120.9(3) . . ?
C8 C7 C6 117.9(4) . . ?
C9 C8 C7 118.8(3) . . ?
C8 C9 C10 118.2(3) . . ?
C11 C10 C9 118.6(3) . . ?
N4 C11 C10 122.9(3) . . ?
C13 C12 C17 119.8(4) . . ?
C13 C12 C1 119.4(4) . . ?
C17 C12 C1 120.7(4) . . ?
C14 C13 C12 120.3(4) . . ?
C13 C14 C15 121.0(5) . . ?
C14 C15 C16 119.1(5) . . ?
C15 C16 C17 120.5(4) . . ?
C12 C17 C16 119.3(4) . . ?
F5 P F2 87.7(2) . . ?
F5 P F6 92.0(2) . . ?
F2 P F6 179.0(2) . . ?
F5 P F3 178.9(2) . . ?
F2 P F3 91.4(2) . . ?
F6 P F3 88.9(2) . . ?
F5 P F4 90.6(2) . . ?
F2 P F4 90.4(2) . . ?
F6 P F4 90.5(2) . . ?
F3 P F4 90.0(2) . . ?
F5 P F1 92.5(2) . . ?
F2 P F1 89.0(2) . . ?
F6 P F1 90.0(2) . . ?
F3 P F1 86.9(2) . . ?
F4 P F1 176.8(2) . . ?
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 N3 1.960(4) . ?
Cu N1 1.982(4) 17 ?
Cu N4 1.993(4) . ?
Cu N2 2.008(4) . ?
N1 C2 1.316(5) . ?
N1 C1 1.372(5) . ?
N1 Cu 1.982(4) 18_545 ?
N2 C1 1.309(5) . ?
N2 C3 1.353(5) . ?
N3 C4 1.327(5) . ?
N3 C5 1.484(5) . ?
N4 C7 1.317(5) . ?
N4 C11 1.309(5) . ?
C1 C12 1.486(6) . ?
C2 C3 1.338(5) . ?
C3 C4 1.391(6) . ?
C5 C6 1.521(5) . ?
C6 C7 1.529(5) . ?
C7 C8 1.399(6) . ?
C8 C9 1.383(6) . ?
C9 C10 1.386(5) . ?
C10 C11 1.371(6) . ?
C12 C13 1.388(6) . ?
C12 C17 1.400(5) . ?
C13 C14 1.382(6) . ?
C14 C15 1.385(6) . ?
C15 C16 1.397(6) . ?
C16 C17 1.401(6) . ?
P F5 1.542(3) . ?
P F2 1.546(3) . ?
P F6 1.550(3) . ?
P F3 1.555(3) . ?
P F4 1.556(4) . ?
P F1 1.560(3) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139134381
