#------------------------------------------------------------------------------
#$Date: 2025-08-21 12:25:49 +0200 (Thu 21 de Aug de 2025) $
#$Revision: 301846 $
#$URL: svn://www.crystallography.net/cod/cif/7/00/67/7006759.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_7006759
loop_
_publ_author_name
'Aakeröy, Christer B'
'Schultheiss, Nate'
'Desper, John'
_publ_section_title
;
 Directed supramolecular assembly of Cu(II)-based "paddlewheels" into
 infinite 1-D chains using structurally bifunctional ligands.
;
_journal_issue                   13
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              1627
_journal_page_last               1635
_journal_paper_doi               10.1039/b513765a
_journal_year                    2006
_chemical_formula_moiety
;
(C10 H10 N4)2 Cu2 (C2 H3 O2)4
;
_chemical_formula_sum            'C28 H32 Cu2 N8 O8'
_chemical_formula_weight         735.70
_chemical_name_common
;bis(2-amino-4-(3-pyridyl)-6-methylpyrimidine) mu-
(OAc)4dicopper(ii)
;
_chemical_name_systematic
;
bis(2-amino-4-(3-pyridyl)-6-methylpyrimidine) mu-(OAc)4dicopper(II)
;
_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                 99.3600(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.0282(5)
_cell_length_b                   10.6399(7)
_cell_length_c                   18.9041(13)
_cell_measurement_reflns_used    9401
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.0
_cell_measurement_theta_min      2.20
_cell_volume                     1593.27(18)
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_collection       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0237
_diffrn_reflns_av_sigmaI/netI    0.0232
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            17891
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         30.00
_diffrn_reflns_theta_min         2.18
_exptl_absorpt_coefficient_mu    1.396
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.825
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.534
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             756
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.553
_refine_diff_density_min         -0.315
_refine_diff_density_rms         0.077
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         4630
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0301
_refine_ls_R_factor_gt           0.0276
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0400P)²+1.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0751
_refine_ls_wR_factor_ref         0.0767
_reflns_number_gt                4270
_reflns_number_total             4630
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b513765a.txt
_cod_data_source_block           7
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7006759
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.462311(19) 0.439494(15) 0.055368(8) 0.01102(6) Uani 1 1 d . . .
N11 N 0.09429(15) 0.53063(11) 0.41833(6) 0.0155(2) Uani 1 1 d . . .
C12 C 0.14818(17) 0.40981(13) 0.42452(7) 0.0153(2) Uani 1 1 d . . .
N12 N 0.13080(18) 0.34958(13) 0.48548(7) 0.0208(3) Uani 1 1 d . . .
H12A H 0.074(3) 0.387(2) 0.5130(11) 0.025 Uiso 1 1 d . . .
H12B H 0.171(3) 0.274(2) 0.4920(11) 0.025 Uiso 1 1 d . . .
N13 N 0.21770(15) 0.34481(11) 0.37516(6) 0.0148(2) Uani 1 1 d . . .
C14 C 0.23682(16) 0.40786(13) 0.31574(7) 0.0132(2) Uani 1 1 d . . .
C15 C 0.19181(18) 0.53398(13) 0.30590(7) 0.0154(2) Uani 1 1 d . . .
H15 H 0.2098 0.5785 0.2642 0.019 Uiso 1 1 calc R . .
C16 C 0.11936(17) 0.59216(13) 0.35964(7) 0.0145(2) Uani 1 1 d . . .
C17 C 0.07116(19) 0.72802(13) 0.35467(8) 0.0199(3) Uani 1 1 d . . .
H17A H -0.0361 0.7396 0.3722 0.030 Uiso 1 1 calc R . .
H17B H 0.0588 0.7555 0.3046 0.030 Uiso 1 1 calc R . .
H17C H 0.1592 0.7780 0.3839 0.030 Uiso 1 1 calc R . .
N21 N 0.40246(14) 0.33167(11) 0.14568(6) 0.0137(2) Uani 1 1 d . . .
C22 C 0.34705(17) 0.39363(13) 0.19912(7) 0.0138(2) Uani 1 1 d . . .
H22 H 0.3352 0.4823 0.1954 0.017 Uiso 1 1 calc R . .
C23 C 0.30597(16) 0.33480(13) 0.25988(7) 0.0132(2) Uani 1 1 d . . .
C24 C 0.32661(18) 0.20462(13) 0.26517(7) 0.0162(2) Uani 1 1 d . . .
H24 H 0.3030 0.1609 0.3062 0.019 Uiso 1 1 calc R . .
C25 C 0.38205(18) 0.14001(13) 0.20962(7) 0.0176(3) Uani 1 1 d . . .
H25 H 0.3950 0.0513 0.2119 0.021 Uiso 1 1 calc R . .
C26 C 0.41840(18) 0.20641(13) 0.15067(7) 0.0162(2) Uani 1 1 d . . .
H26 H 0.4557 0.1616 0.1127 0.019 Uiso 1 1 calc R . .
C31 C 0.59961(16) 0.29669(13) -0.05024(7) 0.0139(2) Uani 1 1 d . . .
O31 O 0.54690(13) 0.29206(10) 0.00921(5) 0.0174(2) Uani 1 1 d . . .
O32 O 0.60947(12) 0.39504(9) -0.08686(5) 0.01516(19) Uani 1 1 d . . .
C32 C 0.65970(19) 0.17496(14) -0.07849(8) 0.0197(3) Uani 1 1 d . . .
H32 H 0.6737 0.1860 -0.1287 0.030 Uiso 1 1 calc R . .
H32B H 0.5763 0.1088 -0.0753 0.030 Uiso 1 1 calc R . .
H32C H 0.7680 0.1511 -0.0499 0.030 Uiso 1 1 calc R . .
C41 C 0.79690(17) 0.53896(12) 0.06778(7) 0.0131(2) Uani 1 1 d . . .
O41 O 0.69467(12) 0.48116(10) 0.10012(5) 0.01548(19) Uani 1 1 d . . .
O42 O 0.76215(12) 0.58161(9) 0.00431(5) 0.01482(19) Uani 1 1 d . . .
C42 C 0.97405(18) 0.55786(14) 0.10690(8) 0.0186(3) Uani 1 1 d . . .
H42 H 0.9854 0.5189 0.1544 0.028 Uiso 1 1 calc R . .
H42B H 0.9978 0.6480 0.1122 0.028 Uiso 1 1 calc R . .
H42C H 1.0542 0.5189 0.0796 0.028 Uiso 1 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'
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'
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
O31 Cu1 O41 89.94(4) . . ?
O31 Cu1 O32 169.36(4) . 3_665 ?
O41 Cu1 O32 88.41(4) . 3_665 ?
O31 Cu1 O42 90.27(4) . 3_665 ?
O41 Cu1 O42 169.22(4) . 3_665 ?
O32 Cu1 O42 89.40(4) 3_665 3_665 ?
O31 Cu1 N21 93.66(4) . . ?
O41 Cu1 N21 95.53(4) . . ?
O32 Cu1 N21 96.96(4) 3_665 . ?
O42 Cu1 N21 95.21(4) 3_665 . ?
O31 Cu1 Cu1 84.03(3) . 3_665 ?
O41 Cu1 Cu1 84.64(3) . 3_665 ?
O32 Cu1 Cu1 85.36(3) 3_665 3_665 ?
O42 Cu1 Cu1 84.67(3) 3_665 3_665 ?
N21 Cu1 Cu1 177.68(3) . 3_665 ?
C16 N11 C12 116.68(12) . . ?
N12 C12 N13 117.34(13) . . ?
N12 C12 N11 116.72(12) . . ?
N13 C12 N11 125.94(12) . . ?
C12 N12 H12A 116.4(14) . . ?
C12 N12 H12B 118.3(14) . . ?
H12A N12 H12B 125(2) . . ?
C14 N13 C12 116.05(12) . . ?
N13 C14 C15 122.12(12) . . ?
N13 C14 C23 116.12(12) . . ?
C15 C14 C23 121.75(12) . . ?
C14 C15 C16 117.37(12) . . ?
C14 C15 H15 121.3 . . ?
C16 C15 H15 121.3 . . ?
N11 C16 C15 121.74(13) . . ?
N11 C16 C17 117.07(12) . . ?
C15 C16 C17 121.16(13) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C26 N21 C22 118.36(12) . . ?
C26 N21 Cu1 123.29(9) . . ?
C22 N21 Cu1 118.35(9) . . ?
N21 C22 C23 123.50(13) . . ?
N21 C22 H22 118.3 . . ?
C23 C22 H22 118.3 . . ?
C22 C23 C24 117.59(12) . . ?
C22 C23 C14 121.01(12) . . ?
C24 C23 C14 121.37(12) . . ?
C25 C24 C23 119.08(12) . . ?
C25 C24 H24 120.5 . . ?
C23 C24 H24 120.5 . . ?
C24 C25 C26 119.34(13) . . ?
C24 C25 H25 120.3 . . ?
C26 C25 H25 120.3 . . ?
N21 C26 C25 122.11(12) . . ?
N21 C26 H26 118.9 . . ?
C25 C26 H26 118.9 . . ?
O32 C31 O31 125.36(13) . . ?
O32 C31 C32 117.67(12) . . ?
O31 C31 C32 116.95(12) . . ?
C31 O31 Cu1 123.52(9) . . ?
C31 O32 Cu1 121.72(8) . 3_665 ?
C31 C32 H32 109.5 . . ?
C31 C32 H32B 109.5 . . ?
H32 C32 H32B 109.5 . . ?
C31 C32 H32C 109.5 . . ?
H32 C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
O41 C41 O42 124.89(13) . . ?
O41 C41 C42 117.67(12) . . ?
O42 C41 C42 117.44(12) . . ?
C41 O41 Cu1 123.19(9) . . ?
C41 O42 Cu1 122.55(9) . 3_665 ?
C41 C42 H42 109.5 . . ?
C41 C42 H42B 109.5 . . ?
H42 C42 H42B 109.5 . . ?
C41 C42 H42C 109.5 . . ?
H42 C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?
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 O31 1.9688(10) . ?
Cu1 O41 1.9694(10) . ?
Cu1 O32 1.9742(10) 3_665 ?
Cu1 O42 1.9771(10) 3_665 ?
Cu1 N21 2.1745(11) . ?
Cu1 Cu1 2.6112(3) 3_665 ?
N11 C16 1.3313(18) . ?
N11 C12 1.3553(18) . ?
C12 N12 1.3454(18) . ?
C12 N13 1.3528(17) . ?
N12 H12A 0.85(2) . ?
N12 H12B 0.87(2) . ?
N13 C14 1.3385(17) . ?
C14 C15 1.3942(19) . ?
C14 C23 1.4893(18) . ?
C15 C16 1.3949(18) . ?
C15 H15 0.9500 . ?
C16 C17 1.4955(19) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
N21 C26 1.3408(18) . ?
N21 C22 1.3414(16) . ?
C22 C23 1.3939(17) . ?
C22 H22 0.9500 . ?
C23 C24 1.3967(19) . ?
C24 C25 1.3876(18) . ?
C24 H24 0.9500 . ?
C25 C26 1.3900(18) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C31 O32 1.2642(17) . ?
C31 O31 1.2646(16) . ?
C31 C32 1.5098(19) . ?
O32 Cu1 1.9742(10) 3_665 ?
C32 H32 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
C41 O41 1.2605(16) . ?
C41 O42 1.2706(17) . ?
C41 C42 1.5060(19) . ?
O42 Cu1 1.9771(10) 3_665 ?
C42 H42 0.9800 . ?
C42 H42B 0.9800 . ?
C42 H42C 0.9800 . ?
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
N12 H12A N11 0.85(2) 2.20(2) 3.0440(17) 174(2) 3_566
N12 H12B O42 0.87(2) 2.11(2) 2.9752(16) 171.3(19) 2_645
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
C16 N11 C12 N12 176.69(13) . . . . ?
C16 N11 C12 N13 -3.2(2) . . . . ?
N12 C12 N13 C14 -178.60(13) . . . . ?
N11 C12 N13 C14 1.3(2) . . . . ?
C12 N13 C14 C15 1.6(2) . . . . ?
C12 N13 C14 C23 -177.28(12) . . . . ?
N13 C14 C15 C16 -2.3(2) . . . . ?
C23 C14 C15 C16 176.47(12) . . . . ?
C12 N11 C16 C15 2.3(2) . . . . ?
C12 N11 C16 C17 -175.92(12) . . . . ?
C14 C15 C16 N11 0.3(2) . . . . ?
C14 C15 C16 C17 178.40(13) . . . . ?
O31 Cu1 N21 C26 -4.38(11) . . . . ?
O41 Cu1 N21 C26 -94.67(11) . . . . ?
O32 Cu1 N21 C26 176.26(11) 3_665 . . . ?
O42 Cu1 N21 C26 86.22(11) 3_665 . . . ?
Cu1 Cu1 N21 C26 -0.7(9) 3_665 . . . ?
O31 Cu1 N21 C22 175.51(10) . . . . ?
O41 Cu1 N21 C22 85.22(10) . . . . ?
O32 Cu1 N21 C22 -3.85(10) 3_665 . . . ?
O42 Cu1 N21 C22 -93.88(10) 3_665 . . . ?
Cu1 Cu1 N21 C22 179(100) 3_665 . . . ?
C26 N21 C22 C23 0.4(2) . . . . ?
Cu1 N21 C22 C23 -179.52(10) . . . . ?
N21 C22 C23 C24 1.0(2) . . . . ?
N21 C22 C23 C14 -176.88(12) . . . . ?
N13 C14 C23 C22 -173.49(12) . . . . ?
C15 C14 C23 C22 7.7(2) . . . . ?
N13 C14 C23 C24 8.73(19) . . . . ?
C15 C14 C23 C24 -170.12(13) . . . . ?
C22 C23 C24 C25 -1.7(2) . . . . ?
C14 C23 C24 C25 176.18(13) . . . . ?
C23 C24 C25 C26 1.1(2) . . . . ?
C22 N21 C26 C25 -1.0(2) . . . . ?
Cu1 N21 C26 C25 178.85(10) . . . . ?
C24 C25 C26 N21 0.3(2) . . . . ?
O32 C31 O31 Cu1 1.92(19) . . . . ?
C32 C31 O31 Cu1 -179.77(9) . . . . ?
O41 Cu1 O31 C31 -86.09(11) . . . . ?
O32 Cu1 O31 C31 -5.1(3) 3_665 . . . ?
O42 Cu1 O31 C31 83.14(11) 3_665 . . . ?
N21 Cu1 O31 C31 178.38(11) . . . . ?
Cu1 Cu1 O31 C31 -1.47(10) 3_665 . . . ?
O31 C31 O32 Cu1 -0.98(19) . . . 3_665 ?
C32 C31 O32 Cu1 -179.28(9) . . . 3_665 ?
O42 C41 O41 Cu1 2.96(19) . . . . ?
C42 C41 O41 Cu1 -176.38(9) . . . . ?
O31 Cu1 O41 C41 81.45(11) . . . . ?
O32 Cu1 O41 C41 -88.04(11) 3_665 . . . ?
O42 Cu1 O41 C41 -9.6(3) 3_665 . . . ?
N21 Cu1 O41 C41 175.12(11) . . . . ?
Cu1 Cu1 O41 C41 -2.55(10) 3_665 . . . ?
O41 C41 O42 Cu1 -1.11(19) . . . 3_665 ?
C42 C41 O42 Cu1 178.23(9) . . . 3_665 ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139152366
