#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/32/54/4325419.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_4325419
loop_
_publ_author_name
'José Sánchez Costa'
'Nuno A. G. Bandeira'
'Boris Le Guennic'
'Vincent Robert'
'Patrick Gamez'
'Guillaume Chastanet'
'Luis Ortiz-Frade'
'Laura Gasque'
_publ_contact_author_address
;
Facultad de Química, Universidad nacional Autónoma de México,
 México 04510, D.F. México
;
_publ_contact_author_email       gasquel@servidor.unam.mx
_publ_contact_author_name        'Gasque, Laura'
_publ_section_title
;
 Coexistence of Intramolecular Ligand-Mediated and Through Hydrogen-Bond
 Magnetic Interactions in a Chain of Dicopper(II) Units
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              5696
_journal_page_last               5705
_journal_paper_doi               10.1021/ic200480d
_journal_volume                  50
_journal_year                    2011
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C24 H32 Cu2 n12 O14'
_chemical_formula_sum            'C24 H32 Cu2 O14 n12'
_chemical_formula_weight         839.7
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2008-05-22T17:35:58-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                96.140(13)
_cell_angle_beta                 100.230(18)
_cell_angle_gamma                107.550(16)
_cell_formula_units_Z            1
_cell_length_a                   7.2780(19)
_cell_length_b                   9.6850(15)
_cell_length_c                   12.372(2)
_cell_measurement_reflns_used    49
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      24.785
_cell_measurement_theta_min      10.625
_cell_measurement_wavelength     0.71073
_cell_volume                     806.2(3)
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR2004 (Giacovazzo et al, 2004)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device       'Siemens P4'
_diffrn_measurement_method       '2θ/ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0649
_diffrn_reflns_av_unetI/netI     0.1259
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -1
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            5081
_diffrn_reflns_theta_full        29
_diffrn_reflns_theta_max         29
_diffrn_reflns_theta_min         2.24
_diffrn_standards_decay_%        9.7
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    1.407
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.73
_exptl_crystal_description       prism
_exptl_crystal_F_000             430
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.728
_refine_diff_density_min         -0.914
_refine_diff_density_rms         0.125
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.989
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         4152
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      0.988
_refine_ls_R_factor_all          0.1514
_refine_ls_R_factor_gt           0.0743
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0926P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.154
_refine_ls_wR_factor_ref         0.1913
_reflns_number_gt                2275
_reflns_number_total             4152
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic200480d_si_002.cif
_cod_data_source_block           cu2dimp
_cod_original_formula_sum        'C24 H32 Cu2 n12 O14'
_cod_database_code               4325419
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
C1 C 0.3094(9) 0.8291(6) 0.1014(5) 0.0370(13) Uani 1 1 d . . .
N4 n 0.2261(8) 0.7907(5) -0.0085(4) 0.0380(11) Uani 1 1 d . . .
H4 H 0.2059 0.7072 -0.0489 0.046 Uiso 1 1 calc R . .
C3 C 0.1785(9) 0.9082(6) -0.0454(4) 0.0328(12) Uani 1 1 d . . .
C4 C 0.2406(8) 1.0149(6) 0.0452(4) 0.0282(11) Uani 1 1 d . . .
C5 C 0.2366(9) 1.1670(6) 0.0668(4) 0.0337(12) Uani 1 1 d . . .
H5A H 0.1495 1.1854 0.0051 0.04 Uiso 1 1 calc R . .
H5B H 0.3681 1.2371 0.0762 0.04 Uiso 1 1 calc R . .
C6 C 0.2137(10) 1.3363(6) 0.2265(4) 0.0387(14) Uani 1 1 d . . .
H6A H 0.1097 1.3752 0.1985 0.046 Uiso 1 1 calc R . .
H6B H 0.3354 1.3957 0.2098 0.046 Uiso 1 1 calc R . .
C7 C 0.2387(9) 1.3423(6) 0.3500(5) 0.0342(12) Uani 1 1 d . . .
C8 C 0.2040(10) 1.4492(6) 0.4182(5) 0.0433(15) Uani 1 1 d . . .
H8 H 0.1581 1.52 0.3886 0.052 Uiso 1 1 calc R . .
C9 C 0.2392(10) 1.4492(7) 0.5327(5) 0.0474(16) Uani 1 1 d . . .
H9 H 0.2195 1.5216 0.5805 0.057 Uiso 1 1 calc R . .
C10 C 0.3022(10) 1.3434(7) 0.5740(5) 0.0456(15) Uani 1 1 d . . .
H10 H 0.3242 1.3419 0.6502 0.055 Uiso 1 1 calc R . .
C11 C 0.3339(9) 1.2366(6) 0.5014(4) 0.0387(13) Uani 1 1 d . . .
H11 H 0.3769 1.1639 0.5297 0.046 Uiso 1 1 calc R . .
C12 C 0.0537(9) 0.9027(6) -0.1563(4) 0.0351(13) Uani 1 1 d . . .
H12A H 0.104 0.8584 -0.2135 0.042 Uiso 1 1 calc R . .
H12B H 0.0676 1.0025 -0.1676 0.042 Uiso 1 1 calc R . .
C13 C 0.3820(12) 0.7303(7) 0.1699(6) 0.0577(19) Uani 1 1 d . . .
H13A H 0.4335 0.7796 0.2458 0.086 Uiso 1 1 calc R . .
H13B H 0.4844 0.7058 0.1411 0.086 Uiso 1 1 calc R . .
H13C H 0.2746 0.6421 0.1668 0.086 Uiso 1 1 calc R . .
N1 n 0.3230(8) 0.9650(5) 0.1368(4) 0.0374(11) Uani 1 1 d . . .
N2 n 0.1621(8) 1.1810(5) 0.1717(3) 0.0328(11) Uani 1 1 d . . .
N3 n 0.3028(7) 1.2374(5) 0.3905(4) 0.0330(10) Uani 1 1 d . . .
N6 n 0.7038(8) 1.1325(6) 0.3782(4) 0.0416(12) Uani 1 1 d . . .
Cu1 Cu 0.32332(12) 1.08511(7) 0.27745(5) 0.0327(2) Uani 1 1 d . . .
O2 O 0.7013(7) 1.2274(5) 0.3183(4) 0.0515(12) Uani 1 1 d . . .
O1 O 0.5356(6) 1.0374(5) 0.3791(3) 0.0402(10) Uani 1 1 d . . .
O3 O 0.8546(8) 1.1251(8) 0.4348(5) 0.0801(19) Uani 1 1 d . . .
O4 O 0.1152(8) 0.8989(5) 0.3329(4) 0.0608(14) Uani 1 1 d D . .
N5 n 0.8092(10) 0.5636(6) 0.1380(5) 0.0553(15) Uani 1 1 d . . .
O6C O 0.8366(9) 0.6936(5) 0.1692(4) 0.0689(16) Uani 1 1 d . A .
O6AA O 0.849(4) 0.5279(14) 0.0546(17) 0.192(9) Uani 0.7 1 d P A 1
O6AB O 0.642(6) 0.493(2) 0.063(3) 0.163(17) Uani 0.3 1 d P A 2
O6BB O 0.853(6) 0.487(3) 0.1854(16) 0.177(12) Uani 0.69(4) 1 d P A 1
O6BA O 0.686(6) 0.465(3) 0.1678(13) 0.12(2) Uani 0.31(4) 1 d P A 2
H1W H 0.1165 0.8954 0.405 0.181 Uiso 1 1 d RD . .
H2W H 0.0227 0.8219 0.2853 0.181 Uiso 1 1 d RD . .
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 0 '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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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
N1 C1 n4 110.4(5) . .
N1 C1 C13 125.8(5) . .
N4 C1 C13 123.7(5) . .
C1 n4 C3 108.4(4) . .
C1 n4 H4 125.8 . .
C3 n4 H4 125.8 . .
C4 C3 n4 104.9(5) . .
C4 C3 C12 129.0(5) . .
N4 C3 C12 125.3(5) . .
C3 C4 n1 110.1(4) . .
C3 C4 C5 134.4(5) . .
N1 C4 C5 115.5(4) . .
C4 C5 n2 106.4(4) . .
C4 C5 H5A 110.5 . .
N2 C5 H5A 110.5 . .
C4 C5 H5B 110.5 . .
N2 C5 H5B 110.5 . .
H5A C5 H5B 108.6 . .
N2 C6 C7 109.0(4) . .
N2 C6 H6A 109.9 . .
C7 C6 H6A 109.9 . .
N2 C6 H6B 109.9 . .
C7 C6 H6B 109.9 . .
H6A C6 H6B 108.3 . .
N3 C7 C8 122.0(5) . .
N3 C7 C6 115.2(5) . .
C8 C7 C6 122.8(5) . .
C7 C8 C9 118.6(6) . .
C7 C8 H8 120.7 . .
C9 C8 H8 120.7 . .
C10 C9 C8 119.8(6) . .
C10 C9 H9 120.1 . .
C8 C9 H9 120.1 . .
C9 C10 C11 119.5(6) . .
C9 C10 H10 120.3 . .
C11 C10 H10 120.3 . .
N3 C11 C10 121.0(6) . .
N3 C11 H11 119.5 . .
C10 C11 H11 119.5 . .
C3 C12 n2 115.2(4) . 2_575
C3 C12 H12A 108.5 . .
N2 C12 H12A 108.5 2_575 .
C3 C12 H12B 108.5 . .
N2 C12 H12B 108.5 2_575 .
H12A C12 H12B 107.5 . .
C1 C13 H13A 109.5 . .
C1 C13 H13B 109.5 . .
H13A C13 H13B 109.5 . .
C1 C13 H13C 109.5 . .
H13A C13 H13C 109.5 . .
H13B C13 H13C 109.5 . .
C1 n1 C4 106.2(4) . .
C1 n1 Cu1 137.8(4) . .
C4 n1 Cu1 110.5(3) . .
C6 n2 C12 112.2(5) . 2_575
C6 n2 C5 112.9(4) . .
C12 n2 C5 113.1(4) 2_575 .
C6 n2 Cu1 106.3(3) . .
C12 n2 Cu1 108.6(3) 2_575 .
C5 n2 Cu1 103.0(3) . .
C7 n3 C11 119.2(5) . .
C7 n3 Cu1 115.6(4) . .
C11 n3 Cu1 125.1(4) . .
O3 n6 O2 123.6(6) . .
O3 n6 O1 119.3(6) . .
O2 n6 O1 117.1(5) . .
N3 Cu1 n1 164.96(19) . .
N3 Cu1 O1 94.90(18) . .
N1 Cu1 O1 98.11(19) . .
N3 Cu1 n2 81.58(18) . .
N1 Cu1 n2 83.96(18) . .
O1 Cu1 n2 165.65(18) . .
N3 Cu1 O4 94.21(19) . .
N1 Cu1 O4 94.45(19) . .
O1 Cu1 O4 84.76(19) . .
N2 Cu1 O4 109.3(2) . .
N6 O1 Cu1 107.9(3) . .
Cu1 O4 H1W 122.1 . .
Cu1 O4 H2W 123.5 . .
H1W O4 H2W 114.4 . .
O6BB n5 O6AA 98.7(15) . .
O6BB n5 O6C 128.1(15) . .
O6AA n5 O6C 119.2(9) . .
O6BB n5 O6BA 58.6(16) . .
O6AA n5 O6BA 114.4(16) . .
O6C n5 O6BA 122(2) . .
O6BB n5 O6AB 110(3) . .
O6AA n5 O6AB 72(2) . .
O6C n5 O6AB 114.9(15) . .
O6BA n5 O6AB 64(2) . .
N5 O6AA O6BB 38.8(8) . .
N5 O6AB O6BA 54.7(16) . .
N5 O6BB O6AA 42.5(9) . .
N5 O6BA O6AB 61.7(17) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 n1 1.311(7) .
C1 n4 1.348(7) .
C1 C13 1.494(8) .
N4 C3 1.385(7) .
N4 H4 0.86 .
C3 C4 1.349(7) .
C3 C12 1.491(8) .
C4 n1 1.389(7) .
C4 C5 1.479(7) .
C5 n2 1.502(7) .
C5 H5A 0.97 .
C5 H5B 0.97 .
C6 n2 1.488(6) .
C6 C7 1.500(8) .
C6 H6A 0.97 .
C6 H6B 0.97 .
C7 n3 1.346(7) .
C7 C8 1.376(8) .
C8 C9 1.394(8) .
C8 H8 0.93 .
C9 C10 1.354(9) .
C9 H9 0.93 .
C10 C11 1.395(8) .
C10 H10 0.93 .
C11 n3 1.351(7) .
C11 H11 0.93 .
C12 n2 1.500(8) 2_575
C12 H12A 0.97 .
C12 H12B 0.97 .
C13 H13A 0.96 .
C13 H13B 0.96 .
C13 H13C 0.96 .
N1 Cu1 1.986(4) .
N2 C12 1.500(8) 2_575
N2 Cu1 2.079(5) .
N3 Cu1 1.980(4) .
N6 O3 1.218(7) .
N6 O2 1.244(7) .
N6 O1 1.293(7) .
Cu1 O1 2.011(4) .
Cu1 O4 2.237(5) .
O4 H1W 0.8946 .
O4 H2W 0.9053 .
N5 O6BB 1.082(13) .
N5 O6AA 1.165(15) .
N5 O6C 1.222(7) .
N5 O6BA 1.233(18) .
N5 O6AB 1.33(3) .
O6AA O6BB 1.71(2) .
O6AB O6BA 1.35(4) .
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
N4 H4 O6BA 0.86 2.5 3.28(4) 152.2 2_665
N4 H4 n5 0.86 2.7 3.542(7) 168 2_665
N4 H4 O6AA 0.86 2.18 2.939(13) 146.8 2_665
N4 H4 O6AB 0.86 2.51 3.22(4) 139.8 2_665
N4 H4 O6BB 0.86 2.27 3.11(2) 168 2_665
O4 H1W n6 0.89 2.85 3.661(7) 152.2 2_676
O4 H1W O3 0.89 1.99 2.883(7) 172.7 2_676
O4 H2W n5 0.91 2.77 3.658(8) 167.3 1_455
O4 H2W O6C 0.91 1.83 2.724(7) 168.1 1_455
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_4
N1 C1 n4 C3 -1.6(7) . .
C13 C1 n4 C3 -179.4(6) . .
C1 n4 C3 C4 1.4(6) . .
C1 n4 C3 C12 -168.9(5) . .
N4 C3 C4 n1 -0.6(6) . .
C12 C3 C4 n1 169.1(6) . .
N4 C3 C4 C5 -179.6(6) . .
C12 C3 C4 C5 -9.8(10) . .
C3 C4 C5 n2 132.8(6) . .
N1 C4 C5 n2 -46.0(6) . .
N2 C6 C7 n3 29.9(7) . .
N2 C6 C7 C8 -151.7(6) . .
N3 C7 C8 C9 0.9(10) . .
C6 C7 C8 C9 -177.4(6) . .
C7 C8 C9 C10 -1.4(10) . .
C8 C9 C10 C11 0.9(10) . .
C9 C10 C11 n3 0.1(10) . .
C4 C3 C12 n2 -97.0(7) . 2_575
N4 C3 C12 n2 70.9(7) . 2_575
N4 C1 n1 C4 1.2(7) . .
C13 C1 n1 C4 178.9(6) . .
N4 C1 n1 Cu1 150.7(5) . .
C13 C1 n1 Cu1 -31.6(11) . .
C3 C4 n1 C1 -0.3(6) . .
C5 C4 n1 C1 178.8(5) . .
C3 C4 n1 Cu1 -159.0(4) . .
C5 C4 n1 Cu1 20.2(6) . .
C7 C6 n2 C12 81.5(6) . 2_575
C7 C6 n2 C5 -149.3(5) . .
C7 C6 n2 Cu1 -37.0(6) . .
C4 C5 n2 C6 160.0(5) . .
C4 C5 n2 C12 -71.3(6) . 2_575
C4 C5 n2 Cu1 45.7(5) . .
C8 C7 n3 C11 0.1(9) . .
C6 C7 n3 C11 178.5(5) . .
C8 C7 n3 Cu1 175.4(5) . .
C6 C7 n3 Cu1 -6.3(7) . .
C10 C11 n3 C7 -0.6(9) . .
C10 C11 n3 Cu1 -175.4(5) . .
C7 n3 Cu1 N1 3.6(11) . .
C11 n3 Cu1 N1 178.5(7) . .
C7 n3 Cu1 O1 153.5(4) . .
C11 n3 Cu1 O1 -31.6(5) . .
C7 n3 Cu1 N2 -12.5(4) . .
C11 n3 Cu1 N2 162.4(5) . .
C7 n3 Cu1 O4 -121.4(4) . .
C11 n3 Cu1 O4 53.5(5) . .
C1 n1 Cu1 N3 -158.2(7) . .
C4 n1 Cu1 N3 -9.5(10) . .
C1 n1 Cu1 O1 52.1(7) . .
C4 n1 Cu1 O1 -159.2(4) . .
C1 n1 Cu1 N2 -142.2(7) . .
C4 n1 Cu1 N2 6.5(4) . .
C1 n1 Cu1 O4 -33.2(7) . .
C4 n1 Cu1 O4 115.5(4) . .
C6 n2 Cu1 N3 27.4(4) . .
C12 n2 Cu1 N3 -93.5(3) 2_575 .
C5 n2 Cu1 N3 146.3(3) . .
C6 n2 Cu1 N1 -148.4(4) . .
C12 n2 Cu1 N1 90.7(3) 2_575 .
C5 n2 Cu1 N1 -29.5(3) . .
C6 n2 Cu1 O1 -49.3(9) . .
C12 n2 Cu1 O1 -170.2(6) 2_575 .
C5 n2 Cu1 O1 69.6(8) . .
C6 n2 Cu1 O4 119.0(4) . .
C12 n2 Cu1 O4 -1.9(3) 2_575 .
C5 n2 Cu1 O4 -122.1(3) . .
O3 n6 O1 Cu1 179.7(5) . .
O2 n6 O1 Cu1 -0.4(6) . .
N3 Cu1 O1 n6 -83.3(4) . .
N1 Cu1 O1 n6 89.2(4) . .
N2 Cu1 O1 n6 -8.2(9) . .
O4 Cu1 O1 n6 -177.1(3) . .
O6C n5 O6AA O6BB 143(2) . .
O6BA n5 O6AA O6BB -59.4(18) . .
O6AB n5 O6AA O6BB -108(3) . .
O6BB n5 O6AB O6BA 38(3) . .
O6AA n5 O6AB O6BA 131(3) . .
O6C n5 O6AB O6BA -115(3) . .
O6C n5 O6BB O6AA -138(2) . .
O6BA n5 O6BB O6AA 113.4(19) . .
O6AB n5 O6BB O6AA 74(2) . .
O6BB n5 O6BA O6AB -138(3) . .
O6AA n5 O6BA O6AB -52(3) . .
O6C n5 O6BA O6AB 104(2) . .
