#------------------------------------------------------------------------------
#$Date: 2016-03-26 03:50:16 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180198 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/94/7109407.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_7109407
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                   16.7208(4)
_cell_length_b                   16.7208(4)
_cell_length_c                   20.8549(8)
_cell_measurement_reflns_used    9810
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      21.91
_cell_measurement_theta_min      2.4
_cell_volume                     5049.6(3)
_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      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0285
_diffrn_reflns_av_sigmaI/netI    0.0170
_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            60872
_diffrn_reflns_theta_full        23.30
_diffrn_reflns_theta_max         23.30
_diffrn_reflns_theta_min         1.41
_exptl_absorpt_coefficient_mu    1.321
_exptl_absorpt_correction_T_max  0.761
_exptl_absorpt_correction_T_min  0.690
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       cubic
_exptl_crystal_F_000             2168
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.933
_refine_diff_density_min         -0.598
_refine_diff_density_rms         0.223
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.01(2)
_refine_ls_extinction_coef       0.0065(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.144
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     358
_refine_ls_number_reflns         4882
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      1.147
_refine_ls_R_factor_all          0.0745
_refine_ls_R_factor_gt           0.0611
_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)+(0.1444P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1637
_refine_ls_wR_factor_ref         0.1831
_reflns_number_gt                4368
_reflns_number_total             4882
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3cc42776e.txt
_cod_data_source_block           wheelr
_cod_original_cell_volume        5049.5(3)
_cod_original_sg_symbol_H-M      P6(3)
_cod_database_code               7109407
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 0.34930(5) 0.27282(5) 0.24904(4) 0.0796(3) Uani 1 1 d .
O1 O 0.4202(4) 0.3142(4) 0.3288(3) 0.1044(15) Uani 1 1 d .
O2 O 0.4384(9) 0.3948(9) 0.4151(4) 0.183(4) Uani 1 1 d .
N2 N 0.3094(3) 0.3562(3) 0.2734(2) 0.0703(11) Uani 1 1 d .
O3 O 0.2659(3) 0.2499(3) 0.1734(2) 0.0819(11) Uani 1 1 d .
C1 C 0.4065(6) 0.3687(6) 0.3623(4) 0.103(2) Uani 1 1 d .
C2 C 0.3442(4) 0.4049(4) 0.3342(3) 0.0742(13) Uani 1 1 d .
H2A H 0.2918 0.3870 0.3631 0.089 Uiso 1 1 calc R
C3 C 0.3946(5) 0.5073(4) 0.3267(3) 0.105(2) Uani 1 1 d .
H3A H 0.3561 0.5202 0.2978 0.126 Uiso 1 1 calc R
C4 C 0.4030(5) 0.5599(4) 0.3859(3) 0.174(6) Uani 1 1 d R
H4A H 0.3435 0.5351 0.4058 0.261 Uiso 1 1 calc R
H4B H 0.4260 0.6237 0.3754 0.261 Uiso 1 1 calc R
H4C H 0.4449 0.5552 0.4150 0.261 Uiso 1 1 calc R
C4' C 0.4851(8) 0.5447(7) 0.2933(6) 0.147(4) Uani 1 1 d .
H4'A H 0.5138 0.6106 0.2900 0.221 Uiso 1 1 calc R
H4'B H 0.4755 0.5185 0.2511 0.221 Uiso 1 1 calc R
H4'C H 0.5245 0.5291 0.3172 0.221 Uiso 1 1 calc R
C5 C 0.2181(4) 0.2857(4) 0.1831(3) 0.0712(14) Uani 1 1 d .
C6 C 0.2413(3) 0.3510(3) 0.2408(3) 0.0665(13) Uani 1 1 d .
O4 O 0.1505(3) 0.2753(3) 0.1480(2) 0.0801(10) Uani 1 1 d .
O5 O 0.1943(3) 0.3887(3) 0.2525(2) 0.0756(9) Uani 1 1 d .
Cu2 Cu 0.25709(5) -0.07741(4) 0.20328(4) 0.0778(3) Uani 1 1 d .
O11 O 0.3380(4) -0.1019(3) 0.1509(3) 0.1053(16) Uani 1 1 d .
O21 O 0.4730(4) -0.0340(4) 0.1020(3) 0.1140(17) Uani 1 1 d .
N21 N 0.3425(3) 0.0468(3) 0.1817(2) 0.0755(12) Uani 1 1 d .
O6 O 0.2045(3) -0.0171(3) 0.2613(2) 0.0886(12) Uani 1 1 d .
C11 C 0.4100(5) -0.0302(5) 0.1280(3) 0.0872(17) Uani 1 1 d .
C21 C 0.4158(5) 0.0617(4) 0.1382(4) 0.0881(18) Uani 1 1 d .
H21A H 0.4754 0.1048 0.1578 0.106 Uiso 1 1 calc R
C31 C 0.4082(8) 0.1001(9) 0.0711(5) 0.135(4) Uani 1 1 d .
H31A H 0.4511 0.0921 0.0434 0.161 Uiso 1 1 calc R
C41 C 0.443(3) 0.193(2) 0.0733(18) 0.33(2) Uani 1 1 d .
H41A H 0.4381 0.2150 0.0315 0.490 Uiso 1 1 calc R
H41B H 0.5061 0.2236 0.0864 0.490 Uiso 1 1 calc R
H41C H 0.4076 0.2069 0.1034 0.490 Uiso 1 1 calc R
C41' C 0.3222(12) 0.0474(16) 0.0425(6) 0.191(7) Uani 1 1 d .
H41D H 0.3216 0.0740 0.0018 0.287 Uiso 1 1 calc R
H41E H 0.2754 0.0465 0.0697 0.287 Uiso 1 1 calc R
H41F H 0.3102 -0.0145 0.0362 0.287 Uiso 1 1 calc R
C51 C 0.2526(4) 0.0703(4) 0.2574(3) 0.0703(13) Uani 1 1 d .
C61 C 0.3373(4) 0.1093(3) 0.2146(3) 0.0699(13) Uani 1 1 d .
O7 O 0.2363(3) 0.1249(3) 0.2861(2) 0.0855(11) Uani 1 1 d .
O8 O 0.3959(3) 0.1952(3) 0.2168(2) 0.0853(11) Uani 1 1 d .
O1W O 0.0000 0.0000 0.4393(6) 0.218(9) Uani 1 3 d S
O2W O 0.1081(6) 0.1641(7) 0.3556(4) 0.160(3) Uani 1 1 d .
O3W O 0.5614(8) 0.4055(11) 0.4932(5) 0.191(4) Uani 1 1 d .
N3 N 0.0873(6) -0.2484(6) 0.9686(3) 0.124(3) Uani 1 1 d D
C12 C 0.0079(15) -0.302(2) 1.0089(10) 0.40(3) Uani 1 1 d D
H12A H -0.0473 -0.3161 0.9858 0.605 Uiso 1 1 calc R
H12B H 0.0123 -0.2668 1.0466 0.605 Uiso 1 1 calc R
H12C H 0.0059 -0.3581 1.0213 0.605 Uiso 1 1 calc R
C13 C 0.1769(13) -0.2269(13) 1.0055(7) 0.190(6) Uani 1 1 d .
H13A H 0.1750 -0.2056 1.0479 0.286 Uiso 1 1 calc R
H13B H 0.2297 -0.1800 0.9831 0.286 Uiso 1 1 calc R
H13C H 0.1813 -0.2819 1.0083 0.286 Uiso 1 1 calc R
C14 C 0.0931(12) -0.2812(12) 0.9058(5) 0.162(5) Uani 1 1 d D
H14A H 0.0392 -0.2943 0.8814 0.243 Uiso 1 1 calc R
H14B H 0.0969 -0.3364 0.9100 0.243 Uiso 1 1 calc R
H14C H 0.1472 -0.2347 0.8842 0.243 Uiso 1 1 calc R
C15 C 0.0834(14) -0.1658(12) 0.9641(9) 0.199(7) Uani 1 1 d D
H15A H 0.0298 -0.1772 0.9401 0.299 Uiso 1 1 calc R
H15B H 0.1379 -0.1193 0.9429 0.299 Uiso 1 1 calc R
H15C H 0.0801 -0.1449 1.0064 0.299 Uiso 1 1 calc R
N4 N 0.0000 0.0000 0.6342(4) 0.0735(19) Uani 1 3 d SD
C16 C 0.0000 0.0000 0.7030(3) 0.108(4) Uani 1 3 d SD
H16A H -0.0210 0.0405 0.7184 0.162 Uiso 0.33 1 calc PR
H16B H 0.0615 0.0210 0.7184 0.162 Uiso 0.33 1 calc PR
H16C H -0.0405 -0.0615 0.7184 0.162 Uiso 0.33 1 calc PR
C17 C 0.0329 -0.0617 0.6105(3) 0.101(2) Uani 1 1 d RD
H17A H 0.0326 -0.0618 0.5644 0.152 Uiso 1 1 calc R
H17B H -0.0071 -0.1232 0.6259 0.152 Uiso 1 1 calc R
H17C H 0.0946 -0.0402 0.6256 0.152 Uiso 1 1 calc R
N5 N 0.3333 -0.3333 0.1523(4) 0.0725(18) Uani 1 3 d SD
C18 C 0.3333 -0.3333 0.2248(8) 0.252(17) Uani 1 3 d SD
H18A H 0.3849 -0.3381 0.2402 0.378 Uiso 0.33 1 calc PR
H18B H 0.2770 -0.3849 0.2402 0.378 Uiso 0.33 1 calc PR
H18C H 0.3382 -0.2770 0.2402 0.378 Uiso 0.33 1 calc PR
C19 C 0.2529(7) -0.3263(8) 0.1381(7) 0.151(4) Uani 1 1 d D
H19A H 0.2458 -0.3257 0.0924 0.226 Uiso 1 1 calc R
H19B H 0.2600 -0.2703 0.1561 0.226 Uiso 1 1 calc R
H19C H 0.1993 -0.3783 0.1561 0.226 Uiso 1 1 calc R
N6 N 0.6667 0.3333 0.3002(12) 0.148(7) Uani 1 3 d SD
C20 C 0.5921(8) 0.2443(7) 0.2947(9) 0.181(6) Uani 1 1 d D
H20A H 0.5790 0.2285 0.2502 0.271 Uiso 1 1 calc R
H20B H 0.5390 0.2410 0.3150 0.271 Uiso 1 1 calc R
H20C H 0.6067 0.2017 0.3151 0.271 Uiso 1 1 calc R
C22 C 0.6667 0.3333 0.3703(15) 0.35(3) Uiso 1 3 d SD
H22A H 0.6082 0.3233 0.3857 0.520 Uiso 0.33 1 calc PR
H22B H 0.7150 0.3918 0.3857 0.520 Uiso 0.33 1 calc PR
H22C H 0.6767 0.2850 0.3857 0.520 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 174.3(2) . .
N2 Cu1 O1 83.4(2) . .
O8 Cu1 O1 99.0(2) . .
N2 Cu1 O3 83.35(19) . .
O8 Cu1 O3 94.19(18) . .
O1 Cu1 O3 166.8(2) . .
N2 Cu1 O7 106.89(18) . .
O8 Cu1 O7 78.01(16) . .
O1 Cu1 O7 96.7(2) . .
O3 Cu1 O7 86.70(17) . .
C1 O1 Cu1 115.5(4) . .
C6 N2 C2 126.0(5) . .
C6 N2 Cu1 115.6(4) . .
C2 N2 Cu1 117.0(4) . .
C5 O3 Cu1 109.6(4) . .
O2 C1 O1 124.2(8) . .
O2 C1 C2 117.7(8) . .
O1 C1 C2 118.1(6) . .
N2 C2 C3 112.9(5) . .
N2 C2 C1 105.6(5) . .
C3 C2 C1 112.4(6) . .
C4 C3 C4' 111.4(5) . .
C4 C3 C2 115.2(4) . .
C4' C3 C2 113.7(7) . .
O3 C5 O4 125.5(5) . .
O3 C5 C6 118.7(5) . .
O4 C5 C6 115.8(5) . .
O5 C6 N2 128.0(6) . .
O5 C6 C5 120.8(5) . .
N2 C6 C5 111.2(5) . .
C5 O4 Cu2 106.5(4) . 2
C6 O5 Cu2 113.0(3) . 2
N21 Cu2 O11 82.8(2) . .
N21 Cu2 O5 160.4(2) . 3
O11 Cu2 O5 99.5(2) . 3
N21 Cu2 O6 82.8(2) . .
O11 Cu2 O6 164.1(2) . .
O5 Cu2 O6 91.96(18) 3 .
N21 Cu2 O4 118.2(2) . 3
O11 Cu2 O4 101.4(2) . 3
O5 Cu2 O4 80.65(16) 3 3
O6 Cu2 O4 91.33(18) . 3
C11 O11 Cu2 115.9(4) . .
C61 N21 C21 126.2(5) . .
C61 N21 Cu2 116.3(4) . .
C21 N21 Cu2 116.7(4) . .
C51 O6 Cu2 110.5(4) . .
O21 C11 O11 123.1(7) . .
O21 C11 C21 120.1(6) . .
O11 C11 C21 116.7(5) . .
N21 C21 C11 107.3(5) . .
N21 C21 C31 113.3(6) . .
C11 C21 C31 108.3(7) . .
C41 C31 C41' 117(2) . .
C41 C31 C21 111(2) . .
C41' C31 C21 113.1(9) . .
O7 C51 O6 125.1(5) . .
O7 C51 C61 118.1(5) . .
O6 C51 C61 116.8(5) . .
O8 C61 N21 127.5(5) . .
O8 C61 C51 119.4(5) . .
N21 C61 C51 113.0(4) . .
C51 O7 Cu1 105.0(4) . .
C61 O8 Cu1 115.3(3) . .
C15 N3 C14 110.8(11) . .
C15 N3 C12 100(2) . .
C14 N3 C12 120.7(14) . .
C15 N3 C13 108.3(12) . .
C14 N3 C13 107.2(10) . .
C12 N3 C13 109.6(16) . .
C16 N4 C17 109.6(4) . 3
C16 N4 C17 109.6(4) . .
C17 N4 C17 109.3(4) 3 .
C16 N4 C17 109.6(4) . 2
C17 N4 C17 109.3(4) 3 2
C17 N4 C17 109.3(4) . 2
C19 N5 C19 115.8(5) . 3_655
C19 N5 C19 115.8(5) . 2_545
C19 N5 C19 115.8(5) 3_655 2_545
C19 N5 C18 102.0(7) . .
C19 N5 C18 102.0(7) 3_655 .
C19 N5 C18 102.0(7) 2_545 .
C20 N6 C20 119.3(4) 2_655 3_665
C20 N6 C20 119.3(4) 2_655 .
C20 N6 C20 119.3(4) 3_665 .
C20 N6 C22 94.7(13) 2_655 .
C20 N6 C22 94.7(13) 3_665 .
C20 N6 C22 94.7(13) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 N2 1.892(5) .
Cu1 O8 1.938(4) .
Cu1 O1 1.957(5) .
Cu1 O3 2.012(4) .
Cu1 O7 2.369(5) .
O1 C1 1.257(10) .
O2 C1 1.207(10) .
N2 C6 1.291(7) .
N2 C2 1.460(8) .
O3 C5 1.230(7) .
C1 C2 1.557(10) .
C2 C3 1.492(9) .
C3 C4 1.4824 .
C3 C4' 1.491(14) .
C5 O4 1.284(7) .
C5 C6 1.538(8) .
C6 O5 1.254(7) .
O4 Cu2 2.240(4) 2
O5 Cu2 1.982(4) 2
Cu2 N21 1.895(5) .
Cu2 O11 1.936(5) .
Cu2 O5 1.982(4) 3
Cu2 O6 2.036(4) .
Cu2 O4 2.240(4) 3
O11 C11 1.293(8) .
O21 C11 1.214(9) .
N21 C61 1.290(8) .
N21 C21 1.442(9) .
O6 C51 1.270(7) .
C11 C21 1.505(10) .
C21 C31 1.572(13) .
C31 C41 1.37(3) .
C31 C41' 1.39(2) .
C51 O7 1.231(7) .
C51 C61 1.519(8) .
C61 O8 1.272(6) .
N3 C15 1.418(14) .
N3 C14 1.441(12) .
N3 C12 1.443(12) .
N3 C13 1.558(18) .
N4 C16 1.435(10) .
N4 C17 1.476(4) 3
N4 C17 1.476(4) .
N4 C17 1.476(4) 2
N5 C19 1.438(7) .
N5 C19 1.438(7) 3_655
N5 C19 1.438(7) 2_545
N5 C18 1.512(17) .
N6 C20 1.389(10) 2_655
N6 C20 1.389(10) 3_665
N6 C20 1.389(10) .
N6 C22 1.46(2) .
