#------------------------------------------------------------------------------
#$Date: 2016-03-26 03:50:16 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180198 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/94/7109406.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_7109406
loop_
_publ_author_name
'Thais Grancha'
'Jesus Ferrando-Soria'
'Joan Cano'
'Francesc Lloret'
'Miguel Julve'
'Giovanni De Munno'
'Donatella Armentano'
'Emilio Pardo'
_publ_section_title
;
 Enantioselective self-assembly of antiferromagnetic hexacopper(II) wheels
 with chiral amino acid oxamates
;
_journal_name_full               Chem.Commun.
_journal_page_first              5942
_journal_paper_doi               10.1039/c3cc42776e
_journal_volume                  49
_journal_year                    2013
_chemical_formula_sum            'C66 H134 Cu6 N12 O37'
_chemical_formula_weight         2069.09
_chemical_name_systematic
;
?
;
_space_group_IT_number           173
_symmetry_cell_setting           hexagonal
_symmetry_space_group_name_Hall  'P 6c'
_symmetry_space_group_name_H-M   'P 63'
_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                120.00
_cell_formula_units_Z            2
_cell_length_a                   16.8745(7)
_cell_length_b                   16.8745(7)
_cell_length_c                   21.0124(14)
_cell_measurement_reflns_used    9790
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      22.91
_cell_measurement_theta_min      2.38
_cell_volume                     5181.7(5)
_computing_cell_refinement       'Bruker APEX'
_computing_data_collection       'Bruker APEX'
_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      293(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  0.0365
_diffrn_reflns_av_sigmaI/netI    0.0194
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            61429
_diffrn_reflns_theta_full        23.06
_diffrn_reflns_theta_max         23.06
_diffrn_reflns_theta_min         1.39
_exptl_absorpt_coefficient_mu    1.288
_exptl_absorpt_correction_T_max  0.8401
_exptl_absorpt_correction_T_min  0.6520
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            BLUE
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       PLATE
_exptl_crystal_F_000             2168
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.920
_refine_diff_density_min         -0.570
_refine_diff_density_rms         0.213
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.02(2)
_refine_ls_extinction_coef       0.0068(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.156
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     361
_refine_ls_number_reflns         4858
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      1.167
_refine_ls_R_factor_all          0.0731
_refine_ls_R_factor_gt           0.0595
_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)+(0.1409P)²+0.2435P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1629
_refine_ls_wR_factor_ref         0.1842
_reflns_number_gt                4343
_reflns_number_total             4858
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3cc42776e.txt
_cod_data_source_block           wheels
_cod_original_cell_volume        5181.6(5)
_cod_original_sg_symbol_H-M      P6(3)
_cod_database_code               7109406
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'-x, -y, z+1/2'
'y, -x+y, z+1/2'
'x-y, x, 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
Cu1 Cu 0.34940(5) 0.07673(5) 0.63380(4) 0.0776(3) Uani 1 1 d .
O1 O 0.4200(4) 0.1071(3) 0.7133(3) 0.1015(15) Uani 1 1 d .
O2 O 0.4380(8) 0.0427(6) 0.8001(4) 0.169(4) Uani 1 1 d .
N2 N 0.3096(3) -0.0467(3) 0.6583(3) 0.0691(12) Uani 1 1 d .
O3 O 0.2653(3) 0.0161(3) 0.5580(2) 0.0809(11) Uani 1 1 d .
C1 C 0.4062(6) 0.0374(6) 0.7478(4) 0.101(2) Uani 1 1 d .
C2 C 0.3439(4) -0.0604(4) 0.7185(3) 0.0725(14) Uani 1 1 d .
H2A H 0.2917 -0.0948 0.7470 0.087 Uiso 1 1 calc R
C3 C 0.3948(7) -0.1132(7) 0.7115(4) 0.106(2) Uani 1 1 d .
H3A H 0.3568 -0.1645 0.6831 0.128 Uiso 1 1 calc R
C4 C 0.4050(11) -0.1551(10) 0.7703(6) 0.161(5) Uani 1 1 d .
H4A H 0.4377 -0.1867 0.7610 0.241 Uiso 1 1 calc R
H4B H 0.3456 -0.1977 0.7868 0.241 Uiso 1 1 calc R
H4C H 0.4383 -0.1082 0.8013 0.241 Uiso 1 1 calc R
C4' C 0.4847(8) -0.0604(11) 0.6787(6) 0.145(4) Uani 1 1 d .
H4'A H 0.4773 -0.0333 0.6406 0.217 Uiso 1 1 calc R
H4'B H 0.5073 -0.1008 0.6678 0.217 Uiso 1 1 calc R
H4'C H 0.5275 -0.0132 0.7064 0.217 Uiso 1 1 calc R
C5 C 0.2184(4) -0.0665(5) 0.5675(3) 0.0710(15) Uani 1 1 d .
C6 C 0.2417(4) -0.1098(4) 0.6257(3) 0.0671(14) Uani 1 1 d .
O4 O 0.1501(3) -0.1242(3) 0.5326(2) 0.0785(11) Uani 1 1 d .
O5 O 0.1943(3) -0.1942(3) 0.6365(2) 0.0726(9) Uani 1 1 d .
Cu2 Cu 0.25667(6) 0.33421(5) 0.58780(4) 0.0752(3) Uani 1 1 d .
O11 O 0.3377(4) 0.4399(4) 0.5352(3) 0.1039(16) Uani 1 1 d .
O21 O 0.4737(4) 0.5079(4) 0.4863(3) 0.1131(18) Uani 1 1 d .
N21 N 0.3418(4) 0.2955(4) 0.5663(3) 0.0757(13) Uani 1 1 d .
O6 O 0.2037(3) 0.2209(3) 0.6456(2) 0.0870(13) Uani 1 1 d .
C11 C 0.4097(5) 0.4408(5) 0.5131(4) 0.0836(17) Uani 1 1 d .
C21 C 0.4154(5) 0.3535(5) 0.5228(4) 0.0867(19) Uani 1 1 d .
H21A H 0.4741 0.3701 0.5429 0.104 Uiso 1 1 calc R
C31 C 0.4103(9) 0.3079(8) 0.4562(6) 0.135(4) Uani 1 1 d .
H31A H 0.4521 0.3601 0.4298 0.162 Uiso 1 1 calc R
C41 C 0.446(3) 0.252(2) 0.4522(15) 0.33(2) Uani 1 1 d .
H41A H 0.4380 0.2278 0.4097 0.501 Uiso 1 1 calc R
H41B H 0.4147 0.2018 0.4816 0.501 Uiso 1 1 calc R
H41C H 0.5098 0.2851 0.4625 0.501 Uiso 1 1 calc R
C41' C 0.3233(13) 0.2763(13) 0.4260(7) 0.197(8) Uani 1 1 d .
H41D H 0.3227 0.2496 0.3856 0.295 Uiso 1 1 calc R
H41E H 0.3132 0.3270 0.4198 0.295 Uiso 1 1 calc R
H41F H 0.2756 0.2313 0.4525 0.295 Uiso 1 1 calc R
C51 C 0.2525(4) 0.1825(4) 0.6425(3) 0.0706(14) Uani 1 1 d .
C61 C 0.3377(4) 0.2283(4) 0.5994(3) 0.0680(14) Uani 1 1 d .
O7 O 0.2359(3) 0.1115(3) 0.6710(2) 0.0849(11) Uani 1 1 d .
O8 O 0.3958(3) 0.2010(3) 0.6012(2) 0.0835(12) Uani 1 1 d .
O1W O 0.0000 0.0000 0.8238(7) 0.217(9) Uani 1 3 d S
O2W O 0.0563(6) 0.1648(7) 0.7405(4) 0.160(3) Uani 1 1 d .
O3W O 0.4071(12) 0.5619(8) 0.3773(5) 0.201(5) Uani 1 1 d .
N3 N 0.0885(6) 0.3368(6) 0.3538(3) 0.126(3) Uani 1 1 d D
C12 C 0.0102(14) 0.316(3) 0.3930(9) 0.32(2) Uani 1 1 d D
H12A H -0.0449 0.2769 0.3698 0.487 Uiso 1 1 calc R
H12B H 0.0114 0.3713 0.4045 0.487 Uiso 1 1 calc R
H12C H 0.0120 0.2847 0.4308 0.487 Uiso 1 1 calc R
C13 C 0.1786(13) 0.4055(14) 0.3893(7) 0.194(7) Uani 1 1 d .
H13A H 0.1783 0.3828 0.4312 0.291 Uiso 1 1 calc R
H13B H 0.1823 0.4640 0.3924 0.291 Uiso 1 1 calc R
H13C H 0.2304 0.4118 0.3661 0.291 Uiso 1 1 calc R
C14 C 0.0924(9) 0.3750(7) 0.2907(4) 0.167(6) Uani 1 1 d D
H14A H 0.0366 0.3363 0.2682 0.251 Uiso 1 1 calc R
H14B H 0.1431 0.3787 0.2674 0.251 Uiso 1 1 calc R
H14C H 0.1001 0.4351 0.2950 0.251 Uiso 1 1 calc R
C15 C 0.0822(9) 0.2500(7) 0.3488(4) 0.212(9) Uani 1 1 d RD
H15A H 0.0270 0.2086 0.3266 0.318 Uiso 1 1 d R
H15B H 0.0811 0.2266 0.3906 0.318 Uiso 1 1 d R
H15C H 0.1341 0.2561 0.3258 0.318 Uiso 1 1 d R
N4 N 0.0000 0.0000 0.5187(4) 0.072(2) Uani 1 3 d SD
C16 C 0.0000 0.0000 0.5875(6) 0.107(4) Uani 1 3 d SD
H16A H -0.0609 -0.0400 0.6028 0.161 Uiso 0.33 1 calc PR
H16B H 0.0209 0.0609 0.6028 0.161 Uiso 0.33 1 calc PR
H16C H 0.0400 -0.0209 0.6028 0.161 Uiso 0.33 1 calc PR
C17 C 0.0951(5) 0.0623(5) 0.4947(4) 0.098(2) Uani 1 1 d D
H17A H 0.0949 0.0622 0.4491 0.147 Uiso 1 1 calc R
H17B H 0.1351 0.0413 0.5099 0.147 Uiso 1 1 calc R
H17C H 0.1162 0.1233 0.5099 0.147 Uiso 1 1 calc R
N5 N 0.3333 0.6667 0.5355(4) 0.0684(19) Uani 1 3 d SD
C18 C 0.3333 0.6667 0.6052(10) 0.248(17) Uani 1 3 d SD
H18A H 0.3846 0.7224 0.6205 0.372 Uiso 0.33 1 calc PR
H18B H 0.3377 0.6154 0.6205 0.372 Uiso 0.33 1 calc PR
H18C H 0.2776 0.6623 0.6205 0.372 Uiso 0.33 1 calc PR
C19 C 0.2524(7) 0.5789(6) 0.5272(8) 0.146(4) Uani 1 1 d D
H19A H 0.2407 0.5662 0.4826 0.219 Uiso 1 1 calc R
H19B H 0.2013 0.5794 0.5467 0.219 Uiso 1 1 calc R
H19C H 0.2613 0.5325 0.5467 0.219 Uiso 1 1 calc R
N6 N 0.6667 0.3333 0.6799(10) 0.145(7) Uani 1 3 d SD
C20 C 0.5911(8) 0.3457(10) 0.6879(10) 0.189(7) Uani 1 1 d D
H20A H 0.5797 0.3477 0.7325 0.284 Uiso 1 1 calc R
H20B H 0.5383 0.2958 0.6683 0.284 Uiso 1 1 calc R
H20C H 0.6035 0.4022 0.6683 0.284 Uiso 1 1 calc R
C22 C 0.6667 0.3333 0.6049(11) 0.39(4) Uiso 1 3 d SD
H22A H 0.7157 0.3251 0.5897 0.581 Uiso 0.33 1 calc PR
H22B H 0.6749 0.3906 0.5897 0.581 Uiso 0.33 1 calc PR
H22C H 0.6094 0.2843 0.5897 0.581 Uiso 0.33 1 calc PR
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
N2 Cu1 O8 174.2(2) . .
N2 Cu1 O1 83.8(2) . .
O8 Cu1 O1 98.8(2) . .
N2 Cu1 O3 83.46(19) . .
O8 Cu1 O3 93.95(19) . .
O1 Cu1 O3 167.3(2) . .
N2 Cu1 O7 106.89(19) . .
O8 Cu1 O7 78.01(16) . .
O1 Cu1 O7 96.5(2) . .
O3 Cu1 O7 86.33(18) . .
C1 O1 Cu1 115.3(4) . .
C6 N2 C2 125.7(5) . .
C6 N2 Cu1 115.8(4) . .
C2 N2 Cu1 117.1(4) . .
C5 O3 Cu1 109.5(4) . .
O2 C1 O1 124.7(8) . .
O2 C1 C2 118.2(8) . .
O1 C1 C2 117.1(6) . .
N2 C2 C3 113.1(5) . .
N2 C2 C1 106.5(5) . .
C3 C2 C1 112.1(6) . .
C4 C3 C4' 110.2(10) . .
C4 C3 C2 115.7(8) . .
C4' C3 C2 113.5(8) . .
O3 C5 O4 125.8(5) . .
O3 C5 C6 119.1(5) . .
O4 C5 C6 115.1(6) . .
O5 C6 N2 129.2(6) . .
O5 C6 C5 120.2(5) . .
N2 C6 C5 110.5(5) . .
C5 O4 Cu2 106.8(4) . 3
C6 O5 Cu2 114.0(4) . 3
N21 Cu2 O11 82.9(2) . .
N21 Cu2 O5 160.5(2) . 2
O11 Cu2 O5 99.2(2) . 2
N21 Cu2 O6 82.7(2) . .
O11 Cu2 O6 164.2(2) . .
O5 Cu2 O6 92.31(18) 2 .
N21 Cu2 O4 118.1(2) . 2
O11 Cu2 O4 101.6(2) . 2
O5 Cu2 O4 80.64(16) 2 2
O6 Cu2 O4 90.83(19) . 2
C11 O11 Cu2 115.9(4) . .
C61 N21 C21 125.2(5) . .
C61 N21 Cu2 116.8(4) . .
C21 N21 Cu2 117.0(4) . .
C51 O6 Cu2 110.5(4) . .
O21 C11 O11 123.9(7) . .
O21 C11 C21 119.4(6) . .
O11 C11 C21 116.7(6) . .
N21 C21 C11 106.6(5) . .
N21 C21 C31 114.1(7) . .
C11 C21 C31 109.7(8) . .
C41 C31 C41' 116(2) . .
C41 C31 C21 117.5(19) . .
C41' C31 C21 111.6(9) . .
O7 C51 O6 124.9(6) . .
O7 C51 C61 118.2(5) . .
O6 C51 C61 116.9(5) . .
O8 C61 N21 127.9(6) . .
O8 C61 C51 119.7(5) . .
N21 C61 C51 112.3(5) . .
C51 O7 Cu1 104.9(4) . .
C61 O8 Cu1 115.4(4) . .
C15 N3 C12 101.5(18) . .
C15 N3 C14 110.6(8) . .
C12 N3 C14 117.5(13) . .
C15 N3 C13 110.1(11) . .
C12 N3 C13 109.9(15) . .
C14 N3 C13 107.0(10) . .
C16 N4 C17 109.6(5) . 3
C16 N4 C17 109.6(5) . 2
C17 N4 C17 109.3(5) 3 2
C16 N4 C17 109.6(5) . .
C17 N4 C17 109.3(5) 3 .
C17 N4 C17 109.3(5) 2 .
C19 N5 C19 118.5(3) . 3_565
C19 N5 C19 118.5(3) . 2_665
C19 N5 C19 118.5(3) 3_565 2_665
C19 N5 C18 97.0(7) . .
C19 N5 C18 97.0(7) 3_565 .
C19 N5 C18 97.0(7) 2_665 .
C20 N6 C20 118.6(4) . 2_655
C20 N6 C20 118.6(4) . 3_665
C20 N6 C20 118.6(4) 2_655 3_665
C20 N6 C22 96.8(10) . .
C20 N6 C22 96.8(10) 2_655 .
C20 N6 C22 96.8(10) 3_665 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 N2 1.912(5) .
Cu1 O8 1.959(4) .
Cu1 O1 1.965(5) .
Cu1 O3 2.036(5) .
Cu1 O7 2.398(5) .
O1 C1 1.300(10) .
O2 C1 1.208(10) .
N2 C6 1.302(8) .
N2 C2 1.458(8) .
O3 C5 1.227(8) .
C1 C2 1.572(10) .
C2 C3 1.522(10) .
C3 C4 1.477(14) .
C3 C4' 1.490(15) .
C5 O4 1.302(8) .
C5 C6 1.572(9) .
C6 O5 1.257(7) .
O4 Cu2 2.260(5) 3
O5 Cu2 1.992(4) 3
Cu2 N21 1.905(5) .
Cu2 O11 1.957(5) .
Cu2 O5 1.991(4) 2
Cu2 O6 2.055(4) .
Cu2 O4 2.260(5) 2
O11 C11 1.295(9) .
O21 C11 1.241(9) .
N21 C61 1.303(9) .
N21 C21 1.457(9) .
O6 C51 1.279(7) .
C11 C21 1.537(10) .
C21 C31 1.577(13) .
C31 C41 1.36(3) .
C31 C41' 1.44(2) .
C51 O7 1.239(7) .
C51 C61 1.540(9) .
C61 O8 1.275(7) .
N3 C15 1.418(12) .
N3 C12 1.442(12) .
N3 C14 1.461(11) .
N3 C13 1.565(18) .
N4 C16 1.446(13) .
N4 C17 1.499(7) 3
N4 C17 1.499(7) 2
N4 C17 1.499(7) .
N5 C19 1.437(9) .
N5 C19 1.437(8) 3_565
N5 C19 1.437(9) 2_665
N5 C18 1.465(19) .
N6 C20 1.402(10) .
N6 C20 1.402(10) 2_655
N6 C20 1.402(10) 3_665
N6 C22 1.577(18) .
