#------------------------------------------------------------------------------
#$Date: 2025-08-21 01:01:10 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301838 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/32/18/4321846.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_4321846
loop_
_publ_author_name
'Richard H. Bode'
'Johan E. Bol'
'Willem L. Driessen'
'Frans B. Hulsbergen'
'Jan Reedijk'
'Anthony L. Spek'
_publ_section_title
;
 Formation of Dinuclear Copper(II) Complexes from a Macrocycle with
 Built-in Pyrazole Groups
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              1239
_journal_page_last               1243
_journal_paper_doi               10.1021/ic9811704
_journal_volume                  38
_journal_year                    1999
_chemical_formula_sum            'C38 H52 Cu2 N16 O14'
_chemical_formula_weight         1084.03
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_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                 121.290(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.5662(5)
_cell_length_b                   20.5522(16)
_cell_length_c                   13.9733(13)
_cell_measurement_temperature    150(2)
_cell_volume                     2347.7(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.973
_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  0.1215
_diffrn_reflns_av_sigmaI/netI    0.1548
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            11257
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         1.97
_exptl_absorpt_coefficient_mu    0.988
_exptl_crystal_colour            blue/green
_exptl_crystal_density_diffrn    1.534
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1124
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.679
_refine_diff_density_min         -0.553
_refine_diff_density_rms         0.105
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.922
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     320
_refine_ls_number_reflns         5386
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.922
_refine_ls_R_factor_all          0.1436
_refine_ls_R_factor_gt           0.0664
_refine_ls_shift/su_max          0.151
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0572P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1304
_refine_ls_wR_factor_ref         0.1507
_reflns_number_gt                2943
_reflns_number_total             5386
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic9811704_1.cif
_cod_data_source_block           shelxl
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0572P)^2^+0.0000P] 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^)+(0.0572P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 

2021-10-24
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum        'C76 H104 Cu4 N32 O28'
_cod_original_formula_units_Z    1
_cod_original_formula_weight     2168.07
_cod_database_code               4321846
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.13199(7) 0.11424(3) 0.29594(4) 0.02035(16) Uani 1 d . . .
C10 C -0.1306(6) 0.0874(2) 0.0753(4) 0.0200(10) Uani 1 d . . .
H10A H -0.1894 0.0769 0.1128 0.024 Uiso 1 calc R . .
H10B H -0.0628 0.0502 0.0836 0.024 Uiso 1 calc R . .
N11 N -0.3529(5) 0.0860(2) -0.2221(3) 0.0240(9) Uani 1 d . . .
N12 N -0.2208(5) 0.06954(19) -0.1209(3) 0.0209(9) Uani 1 d . . .
C13 C -0.2531(6) 0.0971(2) -0.0473(4) 0.0214(11) Uani 1 d . . .
C14 C -0.4040(6) 0.1291(2) -0.1021(4) 0.0263(12) Uani 1 d . . .
H14A H -0.4525 0.1513 -0.0688 0.032 Uiso 1 calc R . .
C15 C -0.4658(6) 0.1214(2) -0.2138(4) 0.0250(11) Uani 1 d . . .
C16 C -0.6228(6) 0.1436(3) -0.3135(4) 0.0367(14) Uani 1 d . . .
H16A H -0.6006 0.1648 -0.3654 0.055 Uiso 1 calc R . .
H16B H -0.6763 0.1734 -0.2901 0.055 Uiso 1 calc R . .
H16C H -0.6924 0.1067 -0.3492 0.055 Uiso 1 calc R . .
C17 C -0.3648(6) 0.0572(3) -0.3209(4) 0.0265(12) Uani 1 d . . .
H17A H -0.2554 0.0491 -0.3062 0.032 Uiso 1 calc R . .
H17B H -0.4173 0.0880 -0.3824 0.032 Uiso 1 calc R . .
C18 C -0.4604(6) -0.0059(3) -0.3554(4) 0.0288(12) Uani 1 d . . .
H18A H -0.5747 0.0034 -0.3836 0.035 Uiso 1 calc R . .
H18B H -0.4528 -0.0255 -0.4157 0.035 Uiso 1 calc R . .
C20 C 0.0808(6) 0.1609(3) 0.0849(4) 0.0251(11) Uani 1 d . . .
H20A H 0.1176 0.2057 0.1020 0.030 Uiso 1 calc R . .
H20B H 0.0175 0.1558 0.0042 0.030 Uiso 1 calc R . .
N21 N 0.2573(5) 0.0843(2) 0.2288(3) 0.0238(9) Uani 1 d . . .
N22 N 0.4009(5) 0.0521(2) 0.2630(3) 0.0256(10) Uani 1 d . . .
C23 C 0.4534(6) 0.0638(3) 0.1925(5) 0.0320(13) Uani 1 d . . .
C24 C 0.3444(6) 0.1048(3) 0.1107(4) 0.0336(13) Uani 1 d . . .
H24A H 0.3502 0.1216 0.0511 0.040 Uiso 1 calc R . .
C25 C 0.2244(6) 0.1159(3) 0.1350(4) 0.0255(10) Uani 1 d . . .
C26 C 0.6091(7) 0.0341(3) 0.2098(6) 0.0484(17) Uani 1 d . . .
H26A H 0.6450 0.0581 0.1675 0.073 Uiso 1 calc R . .
H26B H 0.5893 -0.0103 0.1850 0.073 Uiso 1 calc R . .
H26C H 0.6921 0.0356 0.2878 0.073 Uiso 1 calc R . .
N27 N -0.0215(5) 0.14441(18) 0.1336(3) 0.0191(8) Uani 1 d . . .
C30 C -0.1105(6) 0.2017(2) 0.1396(4) 0.0224(11) Uani 1 d . . .
H30A H -0.2130 0.2068 0.0691 0.027 Uiso 1 calc R . .
H30B H -0.0457 0.2406 0.1526 0.027 Uiso 1 calc R . .
N31 N -0.0333(5) 0.15627(18) 0.3192(3) 0.0210(9) Uani 1 d . . .
C32 C -0.1436(6) 0.1931(2) 0.2331(4) 0.0206(10) Uani 1 d . . .
C33 C -0.2717(6) 0.2229(3) 0.2344(4) 0.0295(12) Uani 1 d . . .
H33A H -0.3465 0.2479 0.1737 0.035 Uiso 1 calc R . .
C34 C -0.2882(7) 0.2155(3) 0.3256(4) 0.0340(13) Uani 1 d . . .
H34A H -0.3745 0.2352 0.3272 0.041 Uiso 1 calc R . .
C35 C -0.1739(7) 0.1781(3) 0.4159(4) 0.0318(13) Uani 1 d . . .
H35A H -0.1815 0.1724 0.4791 0.038 Uiso 1 calc R . .
C36 C -0.0492(6) 0.1496(2) 0.4084(4) 0.0259(11) Uani 1 d . . .
H36A H 0.0276 0.1246 0.4682 0.031 Uiso 1 calc R . .
O40 O 0.3505(5) 0.1558(2) 0.4397(3) 0.0407(10) Uani 1 d . . .
N41 N 0.3946(6) 0.2063(2) 0.4131(4) 0.0438(13) Uani 1 d . . .
O42 O 0.3064(6) 0.2282(2) 0.3171(3) 0.0604(14) Uani 1 d . . .
O43 O 0.5243(7) 0.2302(3) 0.4806(4) 0.105(3) Uani 1 d . . .
O44 O 0.1973(4) 0.04735(17) 0.4244(3) 0.0287(8) Uani 1 d . . .
N45 N 0.0946(5) 0.0010(2) 0.3933(4) 0.0303(10) Uani 1 d . . .
O46 O 0.1158(5) -0.0419(2) 0.4622(3) 0.0484(11) Uani 1 d . . .
O47 O -0.0188(4) -0.00129(18) 0.2951(3) 0.0369(9) Uani 1 d . . .
O50 O -0.0134(7) -0.1510(2) 0.3006(4) 0.0701(15) Uani 1 d . . .
H50 H -0.0031 -0.1154 0.3300 0.105 Uiso 1 calc R . .
C51 C -0.0938(9) -0.1435(4) 0.1844(5) 0.066(2) Uani 1 d . . .
H51A H -0.2044 -0.1297 0.1562 0.099 Uiso 1 calc R . .
H51B H -0.0942 -0.1842 0.1506 0.099 Uiso 1 calc R . .
H51C H -0.0381 -0.1113 0.1665 0.099 Uiso 1 calc R . .
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'
Cu Cu 0.3201 1.2651 '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'
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
N21 Cu1 N31 162.95(15) . . ?
N21 Cu1 N27 80.23(15) . . ?
N31 Cu1 N27 82.87(15) . . ?
N21 Cu1 O44 102.75(15) . . ?
N31 Cu1 O44 93.10(15) . . ?
N27 Cu1 O44 150.77(14) . . ?
N21 Cu1 O40 91.82(16) . . ?
N31 Cu1 O40 98.25(15) . . ?
N27 Cu1 O40 133.68(15) . . ?
O44 Cu1 O40 75.53(14) . . ?
N27 C10 C13 115.2(4) . . ?
C15 N11 N12 113.3(4) . . ?
C15 N11 C17 128.9(4) . . ?
N12 N11 C17 117.3(4) . . ?
C13 N12 N11 103.4(4) . . ?
N12 C13 C14 111.2(4) . . ?
N12 C13 C10 117.6(4) . . ?
C14 C13 C10 131.1(5) . . ?
C15 C14 C13 106.4(4) . . ?
N11 C15 C14 105.7(4) . . ?
N11 C15 C16 122.9(4) . . ?
C14 C15 C16 131.4(5) . . ?
N11 C17 C18 112.8(4) . . ?
N22 C18 C17 112.5(4) 3 . ?
N27 C20 C25 107.9(4) . . ?
C25 N21 N22 105.0(4) . . ?
C25 N21 Cu1 115.0(3) . . ?
N22 N21 Cu1 137.3(3) . . ?
C23 N22 N21 110.4(4) . . ?
C23 N22 C18 130.1(4) . 3 ?
N21 N22 C18 118.9(4) . 3 ?
N22 C23 C24 108.1(5) . . ?
N22 C23 C26 121.8(5) . . ?
C24 C23 C26 130.1(5) . . ?
C23 C24 C25 105.6(5) . . ?
N21 C25 C24 110.9(4) . . ?
N21 C25 C20 116.6(4) . . ?
C24 C25 C20 132.1(4) . . ?
C30 N27 C20 112.2(4) . . ?
C30 N27 C10 113.2(4) . . ?
C20 N27 C10 111.6(4) . . ?
C30 N27 Cu1 106.2(3) . . ?
C20 N27 Cu1 108.1(3) . . ?
C10 N27 Cu1 105.1(3) . . ?
N27 C30 C32 110.0(4) . . ?
C36 N31 C32 118.3(4) . . ?
C36 N31 Cu1 126.7(3) . . ?
C32 N31 Cu1 114.9(3) . . ?
N31 C32 C33 121.8(4) . . ?
N31 C32 C30 114.9(4) . . ?
C33 C32 C30 123.2(4) . . ?
C34 C33 C32 119.7(5) . . ?
C33 C34 C35 119.1(5) . . ?
C36 C35 C34 117.8(5) . . ?
N31 C36 C35 123.3(5) . . ?
N41 O40 Cu1 111.2(3) . . ?
O43 N41 O42 123.0(5) . . ?
O43 N41 O40 118.4(5) . . ?
O42 N41 O40 118.6(5) . . ?
N45 O44 Cu1 111.6(3) . . ?
O47 N45 O46 122.1(5) . . ?
O47 N45 O44 119.1(4) . . ?
O46 N45 O44 118.7(4) . . ?
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
Cu1 N21 1.966(4) . ?
Cu1 N31 1.972(4) . ?
Cu1 N27 2.056(4) . ?
Cu1 O44 2.083(3) . ?
Cu1 O40 2.185(4) . ?
C10 N27 1.498(6) . ?
C10 C13 1.505(6) . ?
N11 C15 1.355(6) . ?
N11 N12 1.362(5) . ?
N11 C17 1.451(6) . ?
N12 C13 1.343(6) . ?
C13 C14 1.398(7) . ?
C14 C15 1.362(6) . ?
C15 C16 1.494(6) . ?
C17 C18 1.515(7) . ?
C18 N22 1.460(6) 3 ?
C20 N27 1.491(6) . ?
C20 C25 1.494(7) . ?
N21 C25 1.345(6) . ?
N21 N22 1.368(5) . ?
N22 C23 1.339(7) . ?
N22 C18 1.459(6) 3 ?
C23 C24 1.366(7) . ?
C23 C26 1.509(8) . ?
C24 C25 1.375(7) . ?
N27 C30 1.481(6) . ?
C30 C32 1.505(7) . ?
N31 C36 1.338(6) . ?
N31 C32 1.348(6) . ?
C32 C33 1.379(7) . ?
C33 C34 1.373(7) . ?
C34 C35 1.396(7) . ?
C35 C36 1.381(7) . ?
O40 N41 1.248(5) . ?
N41 O43 1.206(6) . ?
N41 O42 1.241(6) . ?
O44 N45 1.272(5) . ?
N45 O47 1.231(5) . ?
N45 O46 1.241(5) . ?
O50 C51 1.399(7) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139134382
