#------------------------------------------------------------------------------
#$Date: 2016-03-24 01:59:59 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179550 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/19/4501972.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_4501972
loop_
_publ_author_name
'Thuéry, Pierre'
'Masci, Bernardo'
_publ_section_title
;
 Two- and Three-Dimensional Assemblies Formed by Alkali Metal
 (Li+−Cs+) and Ba2+Ions with
 Bicyclo[2.2.2]oct-7-ene-2,3,5,6-tetracarboxylic Acid
;
_journal_issue                   9
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              4109
_journal_paper_doi               10.1021/cg100785r
_journal_volume                  10
_journal_year                    2010
_chemical_formula_sum            'C12 H18 Na2 O12'
_chemical_formula_weight         400.24
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_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_method           SHELXL-97
_cell_angle_alpha                100.866(4)
_cell_angle_beta                 99.657(4)
_cell_angle_gamma                107.773(3)
_cell_formula_units_Z            2
_cell_length_a                   6.2889(5)
_cell_length_b                   10.3066(7)
_cell_length_c                   13.2245(8)
_cell_measurement_reflns_used    65662
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      25.68
_cell_measurement_theta_min      3.00
_cell_volume                     778.02(10)
_computing_cell_refinement       'HKL2000 (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 1998)'
_computing_data_reduction        'HKL2000 (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
'SHELXTL (Sheldrick, 2008); PLATON (Spek, 2003)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type
'Nonius Kappa-CCD area-detector diffractometer'
_diffrn_measurement_method
'two φ and nine ω scans with 2° steps (692 frames)'
_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  0.0531
_diffrn_reflns_av_sigmaI/netI    0.0574
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_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            65662
_diffrn_reflns_theta_full        25.68
_diffrn_reflns_theta_max         25.68
_diffrn_reflns_theta_min         3.00
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.198
_exptl_absorpt_correction_T_max  0.982
_exptl_absorpt_correction_T_min  0.867
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.708
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       irregular
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.892
_refine_diff_density_min         -0.483
_refine_diff_density_rms         0.146
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         2919
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0936
_refine_ls_R_factor_gt           0.0773
_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)+(0.1523P)²+0.8208P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2060
_refine_ls_wR_factor_ref         0.2146
_reflns_number_gt                2541
_reflns_number_total             2919
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg100785r_si_002.cif
_cod_data_source_block           4
_cod_database_code               4501972
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
Na1 Na 0.2823(2) 0.61423(13) 0.20337(10) 0.0271(4) Uani 1 1 d .
Na2 Na 0.3181(2) 0.27581(13) 0.58457(10) 0.0220(4) Uani 1 1 d .
O1 O 0.4311(4) 0.4946(2) 0.31564(18) 0.0219(5) Uani 1 1 d .
O2 O 0.4031(4) 0.3817(2) 0.44305(17) 0.0215(5) Uani 1 1 d .
O3 O -0.0560(4) 0.2464(2) 0.49531(16) 0.0197(5) Uani 1 1 d .
O4 O -0.0504(4) 0.4157(2) 0.41149(16) 0.0215(5) Uani 1 1 d .
O5 O -0.2660(4) -0.2554(2) 0.24965(18) 0.0240(5) Uani 1 1 d .
O6 O -0.2605(4) -0.2667(2) 0.08000(18) 0.0259(5) Uani 1 1 d .
H6 H -0.1193 -0.2760 0.0819 0.031 Uiso 1 1 d R
O7 O 0.2590(4) -0.1653(2) 0.17262(18) 0.0246(5) Uani 1 1 d .
O8 O 0.2289(4) -0.0934(2) 0.02356(17) 0.0242(5) Uani 1 1 d .
H8 H 0.3142 -0.1329 0.0021 0.029 Uiso 1 1 d R
O9 O 0.3603(4) 0.7831(2) 0.37574(18) 0.0242(5) Uani 1 1 d .
H9A H 0.2635 0.7407 0.4174 0.029 Uiso 1 1 d R
H9B H 0.3187 0.8440 0.3429 0.029 Uiso 1 1 d R
O10 O -0.1085(4) 0.5116(2) 0.22098(18) 0.0247(5) Uani 1 1 d .
H10A H -0.1155 0.4838 0.2799 0.030 Uiso 1 1 d R
H10B H -0.1718 0.5796 0.2235 0.030 Uiso 1 1 d R
O11A O 0.3005(9) 0.5138(5) 0.0459(4) 0.0282(16) Uani 0.517(10) 1 d PU
O11B O 0.1314(11) 0.4637(7) 0.0347(4) 0.0396(19) Uani 0.483(10) 1 d PU
O12 O 0.4077(4) -0.2528(2) -0.07763(18) 0.0270(6) Uani 1 1 d .
H12A H 0.5412 -0.2562 -0.0505 0.032 Uiso 1 1 d R
H12B H 0.3126 -0.3441 -0.1049 0.032 Uiso 1 1 d R
C1 C 0.1671(5) 0.2569(3) 0.2698(2) 0.0170(6) Uani 1 1 d .
H1 H 0.1240 0.2787 0.2019 0.020 Uiso 1 1 calc R
C2 C -0.0572(5) 0.1977(3) 0.3090(2) 0.0163(6) Uani 1 1 d .
H2 H -0.1864 0.1974 0.2558 0.020 Uiso 1 1 calc R
C3 C -0.0972(5) 0.0423(3) 0.3115(2) 0.0170(6) Uani 1 1 d .
H3 H -0.2333 0.0038 0.3381 0.020 Uiso 1 1 calc R
C4 C -0.1306(5) -0.0392(3) 0.1951(2) 0.0174(6) Uani 1 1 d .
H4 H -0.2475 -0.0147 0.1517 0.021 Uiso 1 1 calc R
C5 C 0.0948(5) 0.0178(3) 0.1577(2) 0.0171(6) Uani 1 1 d .
H5 H 0.0592 0.0589 0.0987 0.021 Uiso 1 1 calc R
C6 C 0.2749(5) 0.1390(3) 0.2510(2) 0.0178(6) Uani 1 1 d .
H6A H 0.4220 0.1743 0.2319 0.021 Uiso 1 1 calc R
C7 C 0.3466(5) 0.3890(3) 0.3465(2) 0.0182(6) Uani 1 1 d .
C8 C -0.0546(5) 0.2906(3) 0.4146(2) 0.0175(6) Uani 1 1 d .
C9 C -0.2230(5) -0.1993(3) 0.1749(2) 0.0193(6) Uani 1 1 d .
C10 C 0.2003(5) -0.0912(3) 0.1199(2) 0.0185(6) Uani 1 1 d .
C11 C 0.3057(5) 0.0849(3) 0.3486(2) 0.0188(6) Uani 1 1 d .
H11 H 0.4478 0.0871 0.3844 0.023 Uiso 1 1 calc R
C12 C 0.1136(5) 0.0339(3) 0.3791(2) 0.0176(6) Uani 1 1 d .
H12 H 0.1093 -0.0040 0.4375 0.021 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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Na Na 0.0362 0.0249 '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
O11A Na1 O1 104.29(15) . .
O11B Na1 O1 108.17(17) . .
O11A Na1 O7 99.54(14) . 1_565
O11B Na1 O7 102.05(18) . 1_565
O1 Na1 O7 148.79(10) . 1_565
O11A Na1 O10 108.05(16) . .
O11B Na1 O10 82.62(18) . .
O1 Na1 O10 93.48(9) . .
O7 Na1 O10 98.02(9) 1_565 .
O11A Na1 O9 163.00(16) . .
O11B Na1 O9 167.21(17) . .
O1 Na1 O9 80.59(9) . .
O7 Na1 O9 71.06(8) 1_565 .
O10 Na1 O9 87.63(9) . .
O11A Na1 O5 88.63(16) . 1_665
O11B Na1 O5 114.08(18) . 1_665
O1 Na1 O5 75.52(8) . 1_665
O7 Na1 O5 85.30(8) 1_565 1_665
O10 Na1 O5 162.04(9) . 1_665
O9 Na1 O5 76.71(8) . 1_665
O9 Na2 O5 87.38(9) 2_666 2_556
O9 Na2 O3 156.63(10) 2_666 .
O5 Na2 O3 101.23(9) 2_556 .
O9 Na2 O1 83.60(9) 2_666 2_666
O5 Na2 O1 81.81(9) 2_556 2_666
O3 Na2 O1 118.91(9) . 2_666
O9 Na2 O2 99.14(9) 2_666 .
O5 Na2 O2 159.88(9) 2_556 .
O3 Na2 O2 80.21(8) . .
O1 Na2 O2 80.06(8) 2_666 .
O9 Na2 C12 91.96(9) 2_666 .
O5 Na2 C12 125.01(9) 2_556 .
O3 Na2 C12 65.25(8) . .
O1 Na2 C12 152.71(9) 2_666 .
O2 Na2 C12 74.07(8) . .
C8 Na2 C12 61.35(8) . .
C7 O1 Na1 134.4(2) . .
C7 O1 Na2 129.5(2) . 2_666
Na1 O1 Na2 84.66(8) . 2_666
C7 O2 Na2 150.28(19) . .
C8 O3 Na2 111.16(18) . .
C9 O5 Na2 159.7(2) . 2_556
C9 O5 Na1 106.57(19) . 1_445
Na2 O5 Na1 79.69(8) 2_556 1_445
C9 O6 H6 98.7 . .
C10 O7 Na1 154.7(2) . 1_545
C10 O8 H8 118.7 . .
Na2 O9 Na1 84.11(8) 2_666 .
Na2 O9 H9A 104.5 2_666 .
Na1 O9 H9A 109.4 . .
Na2 O9 H9B 137.1 2_666 .
Na1 O9 H9B 90.7 . .
H9A O9 H9B 117.2 . .
Na1 O10 H10A 113.5 . .
Na1 O10 H10B 107.1 . .
H10A O10 H10B 106.9 . .
H12A O12 H12B 105.9 . .
C7 C1 C6 109.1(2) . .
C7 C1 C2 114.1(2) . .
C6 C1 C2 108.2(2) . .
C7 C1 H1 108.4 . .
C6 C1 H1 108.4 . .
C2 C1 H1 108.4 . .
C8 C2 C3 113.1(2) . .
C8 C2 C1 112.7(2) . .
C3 C2 C1 109.2(2) . .
C8 C2 H2 107.2 . .
C3 C2 H2 107.2 . .
C1 C2 H2 107.2 . .
C12 C3 C2 109.5(2) . .
C12 C3 C4 108.9(2) . .
C2 C3 C4 105.8(2) . .
C12 C3 H3 110.9 . .
C2 C3 H3 110.9 . .
C4 C3 H3 110.9 . .
C9 C4 C3 114.5(2) . .
C9 C4 C5 113.6(2) . .
C3 C4 C5 109.6(2) . .
C9 C4 H4 106.2 . .
C3 C4 H4 106.2 . .
C5 C4 H4 106.2 . .
C10 C5 C4 115.5(2) . .
C10 C5 C6 109.6(2) . .
C4 C5 C6 108.3(2) . .
C10 C5 H5 107.8 . .
C4 C5 H5 107.8 . .
C6 C5 H5 107.8 . .
C11 C6 C1 110.1(2) . .
C11 C6 C5 109.2(2) . .
C1 C6 C5 105.3(2) . .
C11 C6 H6A 110.7 . .
C1 C6 H6A 110.7 . .
C5 C6 H6A 110.7 . .
O1 C7 O2 123.5(3) . .
O1 C7 C1 120.6(3) . .
O2 C7 C1 115.9(2) . .
O3 C8 O4 124.0(3) . .
O3 C8 C2 121.4(3) . .
O4 C8 C2 114.6(2) . .
O6 C9 O5 124.4(3) . .
O6 C9 C4 115.2(3) . .
O5 C9 C4 120.3(3) . .
O7 C10 O8 123.4(3) . .
O7 C10 C5 125.0(3) . .
O8 C10 C5 111.6(2) . .
C12 C11 C6 114.4(3) . .
C12 C11 H11 122.8 . .
C6 C11 H11 122.8 . .
C11 C12 C3 114.5(3) . .
C11 C12 H12 122.7 . .
C3 C12 H12 122.7 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Na1 O11A 2.182(5) .
Na1 O11B 2.318(5) .
Na1 O1 2.352(2) .
Na1 O7 2.425(3) 1_565
Na1 O10 2.431(3) .
Na1 O9 2.465(3) .
Na1 O5 2.651(3) 1_665
Na2 O9 2.291(3) 2_666
Na2 O5 2.309(3) 2_556
Na2 O3 2.349(3) .
Na2 O1 2.383(2) 2_666
Na2 O2 2.393(2) .
Na2 C12 3.094(3) .
Na2 Na1 3.1881(17) 2_666
O1 C7 1.233(4) .
O1 Na2 2.383(2) 2_666
O2 C7 1.290(4) .
O3 C8 1.237(4) .
O4 C8 1.290(4) .
O5 C9 1.263(4) .
O5 Na2 2.309(3) 2_556
O5 Na1 2.651(3) 1_445
O6 C9 1.259(4) .
O6 H6 0.9184 .
O7 C10 1.222(4) .
O7 Na1 2.425(3) 1_545
O8 C10 1.313(4) .
O8 H8 0.8214 .
O9 Na2 2.291(3) 2_666
O9 H9A 0.9516 .
O9 H9B 0.9038 .
O10 H10A 0.8823 .
O10 H10B 0.9039 .
O11A O11B 1.001(7) .
O12 H12A 0.8695 .
O12 H12B 0.9102 .
C1 C7 1.521(4) .
C1 C6 1.563(4) .
C1 C2 1.572(4) .
C1 H1 0.9800 .
C2 C8 1.532(4) .
C2 C3 1.552(4) .
C2 H2 0.9800 .
C3 C12 1.505(4) .
C3 C4 1.555(4) .
C3 H3 0.9800 .
C4 C9 1.526(4) .
C4 C5 1.560(4) .
C4 H4 0.9800 .
C5 C10 1.519(4) .
C5 C6 1.566(4) .
C5 H5 0.9800 .
C6 C11 1.506(4) .
C6 H6A 0.9800 .
C11 C12 1.325(5) .
C11 H11 0.9300 .
C12 H12 0.9300 .
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
O6 H6 O7 0.92 2.30 3.059(3) 140.3 .
O6 H6 O11B 0.92 2.21 2.709(6) 113.6 2
O8 H8 O12 0.82 1.77 2.561(3) 160.0 .
O9 H9A O3 0.95 1.90 2.756(3) 148.6 2_566
O9 H9B O7 0.90 2.20 2.842(3) 127.6 1_565
O10 H10A O4 0.88 2.02 2.883(3) 164.8 .
O10 H10B O5 0.90 1.96 2.850(3) 170.4 1_565
O12 H12A O6 0.87 1.99 2.749(3) 144.4 1_655
O12 H12B O10 0.91 1.99 2.843(3) 154.8 2
