#------------------------------------------------------------------------------
#$Date: 2016-03-23 22:06:20 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179467 $
#$URL: svn://www.crystallography.net/cod/cif/4/33/64/4336433.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_4336433
loop_
_publ_author_name
'Nadia Marino'
'Donatella Armentano'
'Teresa F. Mastropietro'
'Miguel Julve'
'Giovanni De Munno'
'José Martínez-Lillo'
_publ_section_title
;
 Cubane-Type CuII4 and MnII2MnIII2 Complexes Based on Pyridoxine: A
 Versatile Ligand for Metal Assembling
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              11934
_journal_page_last               11943
_journal_paper_doi               10.1021/ic4016355
_journal_volume                  52
_journal_year                    2013
_chemical_formula_sum            'C32 H44 Cl4 Cu4 N4 O14'
_chemical_formula_weight         1104.67
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           43
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'F 2 -2d'
_symmetry_space_group_name_H-M   'F d d 2'
_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                90.00
_cell_formula_units_Z            8
_cell_length_a                   31.315(2)
_cell_length_b                   13.7554(8)
_cell_length_c                   17.9847(8)
_cell_measurement_reflns_used    8967
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.37
_cell_measurement_theta_min      2.60
_cell_volume                     7746.9(8)
_computing_cell_refinement       'Bruker APEX'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0701
_diffrn_reflns_av_sigmaI/netI    0.0384
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            36901
_diffrn_reflns_theta_full        25.82
_diffrn_reflns_theta_max         25.82
_diffrn_reflns_theta_min         1.97
_exptl_absorpt_coefficient_mu    2.516
_exptl_absorpt_correction_T_max  0.9283
_exptl_absorpt_correction_T_min  0.7522
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.894
_exptl_crystal_description       polyhedral
_exptl_crystal_F_000             4480
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.543
_refine_diff_density_min         -0.549
_refine_diff_density_rms         0.080
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.311(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     269
_refine_ls_number_reflns         3728
_refine_ls_number_restraints     233
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0453
_refine_ls_R_factor_gt           0.0343
_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)+(0.0502P)²+3.8363P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0805
_refine_ls_wR_factor_ref         0.0854
_reflns_number_gt                3198
_reflns_number_total             3728
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic4016355_si_002.cif
_cod_data_source_block           cub61
_cod_original_cell_volume        7747.0(8)
_cod_database_code               4336433
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'x+1/4, -y+1/4, z+1/4'
'-x+1/4, y+1/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'x+1/4, -y+3/4, z+3/4'
'-x+1/4, y+3/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'x+3/4, -y+1/4, z+3/4'
'-x+3/4, y+1/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'x+3/4, -y+3/4, z+1/4'
'-x+3/4, y+3/4, z+1/4'
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
Cu1 Cu -0.280325(16) 0.65174(4) 0.15630(2) 0.02381(16) Uani 1 1 d .
Cu2 Cu -0.213994(16) 0.65869(4) 0.27044(2) 0.02218(15) Uani 1 1 d .
N1 N -0.22289(12) 0.6274(3) -0.1158(2) 0.0265(9) Uani 1 1 d DU
H1 H -0.2285 0.6289 -0.1626 0.032 Uiso 1 1 calc R
C1 C -0.25578(14) 0.6239(4) -0.0681(2) 0.0227(9) Uani 1 1 d DU
C2 C -0.24693(12) 0.6236(4) 0.0097(2) 0.0222(10) Uani 1 1 d DU
O1 O -0.28030(9) 0.6185(3) 0.05403(19) 0.0290(8) Uani 1 1 d DU
C3 C -0.20440(13) 0.6242(3) 0.0327(2) 0.0203(9) Uani 1 1 d DU
C4 C -0.17132(13) 0.6268(4) -0.0208(2) 0.0240(9) Uani 1 1 d DU
C5 C -0.18168(13) 0.6286(4) -0.0947(3) 0.0273(10) Uani 1 1 d DU
H5 H -0.1602 0.6307 -0.1304 0.033 Uiso 1 1 calc R
C6 C -0.29999(13) 0.6209(4) -0.0996(3) 0.0344(12) Uani 1 1 d DU
H6A H -0.2985 0.6216 -0.1529 0.052 Uiso 1 1 calc R
H6B H -0.3157 0.6766 -0.0827 0.052 Uiso 1 1 calc R
H6C H -0.3141 0.5627 -0.0834 0.052 Uiso 1 1 calc R
C7 C -0.19335(14) 0.6141(4) 0.1139(3) 0.0294(11) Uani 1 1 d DU
H7A H -0.1959 0.5463 0.1280 0.035 Uiso 1 1 calc R
H7B H -0.1638 0.6332 0.1211 0.035 Uiso 1 1 calc R
O2 O -0.21949(8) 0.6706(2) 0.1609(2) 0.0215(7) Uani 1 1 d DU
C8 C -0.12522(13) 0.6264(4) 0.0028(3) 0.0336(11) Uani 1 1 d DU
H8A H -0.1192 0.6837 0.0325 0.040 Uiso 1 1 calc R
H8B H -0.1195 0.5694 0.0330 0.040 Uiso 1 1 calc R
O3 O -0.09864(12) 0.6256(4) -0.0612(2) 0.0590(12) Uani 1 1 d DU
H2 H -0.0735 0.6251 -0.0483 0.089 Uiso 1 1 calc R
N11 N -0.27042(12) 0.6269(3) 0.5411(2) 0.0296(9) Uani 1 1 d DU
H11 H -0.2646 0.6272 0.5878 0.036 Uiso 1 1 calc R
C11 C -0.23729(14) 0.6253(4) 0.4938(2) 0.0274(10) Uani 1 1 d DU
C21 C -0.24688(13) 0.6231(4) 0.4162(2) 0.0241(10) Uani 1 1 d DU
O11 O -0.21421(9) 0.6188(3) 0.37136(19) 0.0331(8) Uani 1 1 d DU
C31 C -0.29001(13) 0.6235(4) 0.3942(3) 0.0244(9) Uani 1 1 d DU
C41 C -0.32268(14) 0.6268(4) 0.4479(3) 0.0265(9) Uani 1 1 d DU
C51 C -0.31116(14) 0.6280(4) 0.5223(3) 0.0310(10) Uani 1 1 d DU
H51 H -0.3321 0.6297 0.5590 0.037 Uiso 1 1 calc R
C61 C -0.19333(15) 0.6189(4) 0.5221(4) 0.0384(13) Uani 1 1 d DU
H61A H -0.1937 0.6214 0.5754 0.058 Uiso 1 1 calc R
H61B H -0.1769 0.6723 0.5031 0.058 Uiso 1 1 calc R
H61C H -0.1807 0.5587 0.5062 0.058 Uiso 1 1 calc R
C71 C -0.30154(15) 0.6101(4) 0.3132(3) 0.0273(11) Uani 1 1 d DU
H71A H -0.2981 0.5421 0.3002 0.033 Uiso 1 1 calc R
H71B H -0.3314 0.6270 0.3063 0.033 Uiso 1 1 calc R
O21 O -0.27604(9) 0.6679(2) 0.2641(2) 0.0197(7) Uani 1 1 d DU
C81 C -0.36854(14) 0.6283(4) 0.4261(3) 0.0379(12) Uani 1 1 d DU
H81A H -0.3738 0.6833 0.3937 0.046 Uiso 1 1 calc R
H81B H -0.3753 0.5694 0.3988 0.046 Uiso 1 1 calc R
O31 O -0.39502(12) 0.6349(4) 0.4895(2) 0.0629(13) Uani 1 1 d DU
H21 H -0.4201 0.6360 0.4765 0.094 Uiso 1 1 calc R
O1W O -0.34361(10) 0.6429(3) 0.1599(2) 0.0376(8) Uani 1 1 d D
H1W H -0.3572(13) 0.629(3) 0.1215(17) 0.056 Uiso 1 1 d D
H2W H -0.3581(13) 0.684(3) 0.182(2) 0.056 Uiso 1 1 d D
Cl1 Cl -0.14153(3) 0.66567(10) 0.26743(8) 0.0376(3) Uani 1 1 d .
Cl2 Cl -0.24699(5) 0.59203(10) -0.28764(10) 0.0570(3) Uani 1 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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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
O1 Cu1 O2 94.23(15) . .
O1 Cu1 O21 171.58(16) . .
O2 Cu1 O21 82.77(15) . .
O1 Cu1 O1W 90.97(15) . .
O2 Cu1 O1W 173.96(17) . .
O21 Cu1 O1W 92.50(14) . .
O1 Cu1 O2 105.91(16) . 14_465
O2 Cu1 O2 82.32(11) . 14_465
O21 Cu1 O2 81.55(13) . 14_465
O1W Cu1 O2 93.31(13) . 14_465
O1 Cu1 Cu2 133.58(10) . .
O2 Cu1 Cu2 42.41(13) . .
O21 Cu1 Cu2 41.51(8) . .
O1W Cu1 Cu2 133.52(12) . .
O2 Cu1 Cu2 86.86(9) 14_465 .
O1 Cu1 Cu1 101.38(11) . 14_465
O2 Cu1 Cu1 47.21(9) . 14_465
O21 Cu1 Cu1 82.39(9) . 14_465
O1W Cu1 Cu1 128.57(11) . 14_465
O2 Cu1 Cu1 35.27(6) 14_465 14_465
Cu2 Cu1 Cu1 64.186(17) . 14_465
O1 Cu1 Cu2 142.08(12) . 14_465
O2 Cu1 Cu2 85.46(10) . 14_465
O21 Cu1 Cu2 45.76(9) . 14_465
O1W Cu1 Cu2 88.55(11) . 14_465
O2 Cu1 Cu2 36.37(10) 14_465 14_465
Cu2 Cu1 Cu2 65.07(2) . 14_465
Cu1 Cu1 Cu2 52.321(14) 14_465 14_465
O11 Cu2 O21 94.08(14) . .
O11 Cu2 O2 166.88(15) . .
O21 Cu2 O2 81.39(13) . .
O11 Cu2 Cl1 92.21(10) . .
O21 Cu2 Cl1 172.25(11) . .
O2 Cu2 Cl1 93.41(9) . .
O11 Cu2 O21 109.35(15) . 14_465
O21 Cu2 O21 78.68(12) . 14_465
O2 Cu2 O21 81.97(12) . 14_465
Cl1 Cu2 O21 94.96(8) . 14_465
O11 Cu2 Cu1 131.34(10) . .
O21 Cu2 Cu1 41.66(12) . .
O2 Cu2 Cu1 40.85(8) . .
Cl1 Cu2 Cu1 134.00(4) . .
O21 Cu2 Cu1 84.67(8) 14_465 .
O11 Cu2 Cu1 144.89(12) . 14_465
O21 Cu2 Cu1 81.93(10) . 14_465
O2 Cu2 Cu1 46.96(8) . 14_465
Cl1 Cu2 Cu1 90.32(4) . 14_465
O21 Cu2 Cu1 35.59(10) 14_465 14_465
Cu1 Cu2 Cu1 63.49(2) . 14_465
O11 Cu2 Cu2 102.30(11) . 14_465
O21 Cu2 Cu2 44.45(9) . 14_465
O2 Cu2 Cu2 83.15(8) . 14_465
Cl1 Cu2 Cu2 129.47(5) . 14_465
O21 Cu2 Cu2 34.55(7) 14_465 14_465
Cu1 Cu2 Cu2 63.222(16) . 14_465
Cu1 Cu2 Cu2 51.710(14) 14_465 14_465
C1 N1 C5 123.9(4) . .
C1 N1 H1 118.1 . .
C5 N1 H1 118.1 . .
N1 C1 C2 118.5(4) . .
N1 C1 C6 118.0(4) . .
C2 C1 C6 123.4(4) . .
O1 C2 C3 125.3(4) . .
O1 C2 C1 116.1(4) . .
C3 C2 C1 118.5(4) . .
C2 O1 Cu1 125.1(3) . .
C2 C3 C4 119.8(4) . .
C2 C3 C7 120.5(4) . .
C4 C3 C7 119.6(4) . .
C5 C4 C3 119.2(4) . .
C5 C4 C8 120.1(4) . .
C3 C4 C8 120.7(4) . .
N1 C5 C4 120.0(4) . .
N1 C5 H5 120.0 . .
C4 C5 H5 120.0 . .
C1 C6 H6A 109.5 . .
C1 C6 H6B 109.5 . .
H6A C6 H6B 109.5 . .
C1 C6 H6C 109.5 . .
H6A C6 H6C 109.5 . .
H6B C6 H6C 109.5 . .
O2 C7 C3 113.4(4) . .
O2 C7 H7A 108.9 . .
C3 C7 H7A 108.9 . .
O2 C7 H7B 108.9 . .
C3 C7 H7B 108.9 . .
H7A C7 H7B 107.7 . .
C7 O2 Cu1 118.3(3) . .
C7 O2 Cu2 120.0(3) . .
Cu1 O2 Cu2 96.75(16) . .
C7 O2 Cu1 122.1(3) . 14_465
Cu1 O2 Cu1 97.51(11) . 14_465
Cu2 O2 Cu1 96.67(13) . 14_465
O3 C8 C4 109.5(4) . .
O3 C8 H8A 109.8 . .
C4 C8 H8A 109.8 . .
O3 C8 H8B 109.8 . .
C4 C8 H8B 109.8 . .
H8A C8 H8B 108.2 . .
C8 O3 H2 109.5 . .
C51 N11 C11 125.8(4) . .
C51 N11 H11 117.1 . .
C11 N11 H11 117.1 . .
N11 C11 C21 117.2(4) . .
N11 C11 C61 120.4(4) . .
C21 C11 C61 122.3(4) . .
O11 C21 C31 125.3(4) . .
O11 C21 C11 116.1(4) . .
C31 C21 C11 118.5(4) . .
C21 O11 Cu2 125.6(3) . .
C21 C31 C41 120.2(4) . .
C21 C31 C71 120.0(4) . .
C41 C31 C71 119.4(4) . .
C51 C41 C31 118.3(4) . .
C51 C41 C81 120.3(4) . .
C31 C41 C81 121.4(4) . .
N11 C51 C41 119.9(4) . .
N11 C51 H51 120.1 . .
C41 C51 H51 120.1 . .
C11 C61 H61A 109.5 . .
C11 C61 H61B 109.5 . .
H61A C61 H61B 109.5 . .
C11 C61 H61C 109.5 . .
H61A C61 H61C 109.5 . .
H61B C61 H61C 109.5 . .
O21 C71 C31 113.1(4) . .
O21 C71 H71A 109.0 . .
C31 C71 H71A 109.0 . .
O21 C71 H71B 109.0 . .
C31 C71 H71B 109.0 . .
H71A C71 H71B 107.8 . .
C71 O21 Cu2 118.9(3) . .
C71 O21 Cu1 120.7(3) . .
Cu2 O21 Cu1 96.83(15) . .
C71 O21 Cu2 116.7(3) . 14_465
Cu2 O21 Cu2 101.00(12) . 14_465
Cu1 O21 Cu2 98.66(14) . 14_465
O31 C81 C41 110.7(4) . .
O31 C81 H81A 109.5 . .
C41 C81 H81A 109.5 . .
O31 C81 H81B 109.5 . .
C41 C81 H81B 109.5 . .
H81A C81 H81B 108.1 . .
C81 O31 H21 109.5 . .
Cu1 O1W H1W 120(3) . .
Cu1 O1W H2W 121(3) . .
H1W O1W H2W 106.1(17) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 O1 1.896(3) .
Cu1 O2 1.924(3) .
Cu1 O21 1.956(4) .
Cu1 O1W 1.987(3) .
Cu1 O2 2.446(3) 14_465
Cu1 Cu2 2.9219(6) .
Cu1 Cu1 3.3038(11) 14_465
Cu1 Cu2 3.3235(6) 14_465
Cu2 O11 1.896(3) .
Cu2 O21 1.950(3) .
Cu2 O2 1.984(4) .
Cu2 Cl1 2.2719(11) .
Cu2 O21 2.408(3) 14_465
Cu2 Cu1 3.3235(6) 14_465
Cu2 Cu2 3.3758(11) 14_465
N1 C1 1.341(5) .
N1 C5 1.345(5) .
N1 H1 0.8600 .
C1 C2 1.426(6) .
C1 C6 1.497(6) .
C2 O1 1.317(5) .
C2 C3 1.395(5) .
C3 C4 1.414(6) .
C3 C7 1.506(6) .
C4 C5 1.369(6) .
C4 C8 1.505(5) .
C5 H5 0.9300 .
C6 H6A 0.9600 .
C6 H6B 0.9600 .
C6 H6C 0.9600 .
C7 O2 1.411(5) .
C7 H7A 0.9700 .
C7 H7B 0.9700 .
O2 Cu1 2.446(3) 14_465
C8 O3 1.421(5) .
C8 H8A 0.9700 .
C8 H8B 0.9700 .
O3 H2 0.8200 .
N11 C51 1.320(6) .
N11 C11 1.342(5) .
N11 H11 0.8600 .
C11 C21 1.428(6) .
C11 C61 1.470(6) .
C21 O11 1.304(5) .
C21 C31 1.408(6) .
C31 C41 1.408(6) .
C31 C71 1.511(6) .
C41 C51 1.386(6) .
C41 C81 1.489(6) .
C51 H51 0.9300 .
C61 H61A 0.9600 .
C61 H61B 0.9600 .
C61 H61C 0.9600 .
C71 O21 1.432(5) .
C71 H71A 0.9700 .
C71 H71B 0.9700 .
O21 Cu2 2.408(3) 14_465
C81 O31 1.413(6) .
C81 H81A 0.9700 .
C81 H81B 0.9700 .
O31 H21 0.8200 .
O1W H1W 0.834(10) .
O1W H2W 0.831(10) .
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
N1 H1 Cl2 0.86 2.38 3.219(4) 166.0 .
N11 H11 Cl2 0.86 2.36 3.202(4) 167.8 1_556
O3 H2 Cl2 0.82 2.45 3.242(4) 163.8 3_565
O31 H21 Cl2 0.82 2.44 3.246(4) 167.9 11_465
O1W H1W Cl1 0.834(10) 2.243(10) 3.076(3) 177(4) 11_464
O1W H2W Cl1 0.831(10) 2.57(2) 3.300(4) 147(4) 14_465
