#------------------------------------------------------------------------------
#$Date: 2016-03-24 01:59:59 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179550 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/19/4501973.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_4501973
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 H16 K2 O11'
_chemical_formula_weight         414.45
_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                105.160(4)
_cell_angle_beta                 91.515(5)
_cell_angle_gamma                94.437(4)
_cell_formula_units_Z            2
_cell_length_a                   8.0763(6)
_cell_length_b                   9.5108(6)
_cell_length_c                   10.4739(9)
_cell_measurement_reflns_used    33527
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      25.68
_cell_measurement_theta_min      2.53
_cell_volume                     773.29(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 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type
'Nonius Kappa-CCD area-detector diffractometer'
_diffrn_measurement_method
'two φ and nine ω scans with 2° steps (573 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  0.0429
_diffrn_reflns_av_sigmaI/netI    0.0481
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            33527
_diffrn_reflns_theta_full        25.68
_diffrn_reflns_theta_max         25.68
_diffrn_reflns_theta_min         2.53
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.674
_exptl_absorpt_correction_T_max  0.960
_exptl_absorpt_correction_T_min  0.760
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.780
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             428
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.292
_refine_diff_density_min         -0.368
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         2932
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0408
_refine_ls_R_factor_gt           0.0322
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0392P)²+0.2359P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0782
_refine_ls_wR_factor_ref         0.0817
_reflns_number_gt                2516
_reflns_number_total             2932
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg100785r_si_002.cif
_cod_data_source_block           5
_cod_database_code               4501973
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
K1 K 0.17914(5) 0.26417(5) 0.24554(4) 0.02378(13) Uani 1 1 d .
K2 K -0.29411(5) 0.20697(5) 0.32550(5) 0.02660(13) Uani 1 1 d .
O1 O -0.03218(17) 0.01399(15) 0.25040(15) 0.0283(3) Uani 1 1 d .
O2 O -0.09860(16) -0.14089(15) 0.37074(14) 0.0250(3) Uani 1 1 d .
H2 H -0.1779 -0.0724 0.4158 0.030 Uiso 1 1 d R
O3 O 0.36286(17) 0.09825(14) 0.37274(13) 0.0241(3) Uani 1 1 d .
O4 O 0.27127(16) -0.04361(15) 0.50018(13) 0.0243(3) Uani 1 1 d .
O5 O 0.47852(15) -0.29503(15) -0.15130(13) 0.0228(3) Uani 1 1 d .
O6 O 0.67719(15) -0.32328(14) -0.01310(13) 0.0216(3) Uani 1 1 d .
O7 O 0.10492(16) -0.38960(15) -0.20201(14) 0.0240(3) Uani 1 1 d .
O8 O 0.24424(15) -0.56900(14) -0.16693(13) 0.0213(3) Uani 1 1 d .
H8 H 0.2812 -0.6046 -0.0906 0.026 Uiso 1 1 d R
O9 O 0.00051(17) 0.32853(16) 0.47460(15) 0.0286(3) Uani 1 1 d .
H9A H 0.0244 0.2766 0.5347 0.034 Uiso 1 1 d R
H9B H -0.0545 0.3903 0.5221 0.034 Uiso 1 1 d R
O10 O 0.29560(17) 0.53030(16) 0.43164(16) 0.0320(3) Uani 1 1 d .
H10A H 0.3133 0.4724 0.4880 0.038 Uiso 1 1 d R
H10B H 0.3972 0.5678 0.4117 0.038 Uiso 1 1 d R
O11 O 0.39228(16) 0.34514(15) 0.58645(14) 0.0271(3) Uani 1 1 d .
H11A H 0.3672 0.2568 0.5371 0.033 Uiso 1 1 d R
H11B H 0.3308 0.3565 0.6587 0.033 Uiso 1 1 d R
C1 C 0.1121(2) -0.2064(2) 0.22081(19) 0.0187(4) Uani 1 1 d .
H1 H 0.0780 -0.2993 0.2405 0.022 Uiso 1 1 calc R
C2 C 0.2977(2) -0.1612(2) 0.27564(19) 0.0194(4) Uani 1 1 d .
H2A H 0.3333 -0.2406 0.3107 0.023 Uiso 1 1 calc R
C3 C 0.4080(2) -0.1544(2) 0.15850(18) 0.0187(4) Uani 1 1 d .
H3 H 0.5225 -0.1180 0.1903 0.022 Uiso 1 1 calc R
C4 C 0.4015(2) -0.3131(2) 0.06578(18) 0.0176(4) Uani 1 1 d .
H4 H 0.4400 -0.3770 0.1181 0.021 Uiso 1 1 calc R
C5 C 0.2155(2) -0.3646(2) 0.01963(18) 0.0184(4) Uani 1 1 d .
H5 H 0.1803 -0.4373 0.0669 0.022 Uiso 1 1 calc R
C6 C 0.1075(2) -0.2356(2) 0.06813(19) 0.0190(4) Uani 1 1 d .
H6 H -0.0068 -0.2616 0.0308 0.023 Uiso 1 1 calc R
C7 C -0.0120(2) -0.0988(2) 0.28169(19) 0.0195(4) Uani 1 1 d .
C8 C 0.3148(2) -0.0234(2) 0.38975(19) 0.0196(4) Uani 1 1 d .
C9 C 0.5238(2) -0.31271(19) -0.04374(19) 0.0189(4) Uani 1 1 d .
C10 C 0.1862(2) -0.4402(2) -0.12647(19) 0.0196(4) Uani 1 1 d .
C11 C 0.1825(2) -0.1023(2) 0.03214(19) 0.0210(4) Uani 1 1 d .
H11 H 0.1260 -0.0548 -0.0205 0.025 Uiso 1 1 calc R
C12 C 0.3359(2) -0.0581(2) 0.08174(19) 0.0208(4) Uani 1 1 d .
H12 H 0.3942 0.0255 0.0702 0.025 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'
K K 0.2009 0.2494 '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
O7 K1 O9 69.82(4) 2 .
O7 K1 O3 152.50(4) 2 .
O9 K1 O3 85.75(4) . .
O7 K1 O1 86.52(4) 2 .
O9 K1 O1 71.23(4) . .
O3 K1 O1 73.39(4) . .
O7 K1 O10 88.83(4) 2 .
O9 K1 O10 65.94(4) . .
O3 K1 O10 92.63(4) . .
O1 K1 O10 135.78(4) . .
O7 K1 O6 91.41(4) 2 2_655
O9 K1 O6 154.89(4) . 2_655
O3 K1 O6 115.48(4) . 2_655
O1 K1 O6 125.81(4) . 2_655
O10 K1 O6 98.23(4) . 2_655
O7 K1 O5 131.56(4) 2 2_655
O9 K1 O5 141.70(4) . 2_655
O3 K1 O5 75.69(4) . 2_655
O1 K1 O5 131.47(4) . 2_655
O10 K1 O5 81.54(4) . 2_655
O6 K1 O5 44.23(3) 2_655 2_655
O5 K2 O4 148.88(4) 2 2_556
O5 K2 O9 132.61(4) 2 .
O4 K2 O9 76.85(4) 2_556 .
O5 K2 O7 68.24(4) 2 2
O4 K2 O7 142.78(4) 2_556 2
O9 K2 O7 68.66(4) . 2
O5 K2 O1 123.26(4) 2 .
O4 K2 O1 71.02(4) 2_556 .
O9 K2 O1 69.99(4) . .
O7 K2 O1 84.11(4) 2 .
O5 K2 O3 77.63(4) 2 1_455
O4 K2 O3 71.86(4) 2_556 1_455
O9 K2 O3 138.06(4) . 1_455
O7 K2 O3 145.04(4) 2 1_455
O1 K2 O3 122.47(4) . 1_455
O5 K2 O10 100.63(4) 2 2_566
O4 K2 O10 86.18(4) 2_556 2_566
O9 K2 O10 59.04(4) . 2_566
O7 K2 O10 87.84(4) 2 2_566
O1 K2 O10 127.69(4) . 2_566
O3 K2 O10 91.29(4) 1_455 2_566
C7 O1 K1 134.22(12) . .
C7 O1 K2 127.92(11) . .
K1 O1 K2 87.48(4) . .
C7 O2 H2 115.6 . .
C8 O3 K1 126.01(11) . .
C8 O3 K2 128.04(11) . 1_655
K1 O3 K2 99.64(4) . 1_655
C8 O4 K2 146.75(11) . 2_556
C9 O5 K2 158.26(12) . 2
C9 O5 K1 95.10(11) . 2_655
K2 O5 K1 102.85(4) 2 2_655
C9 O6 K1 97.92(10) . 2_655
C10 O7 K1 147.14(12) . 2
C10 O7 K2 114.30(11) . 2
K1 O7 K2 90.94(4) 2 2
C10 O8 H8 111.0 . .
K1 O9 K2 90.21(5) . .
K1 O9 H9A 115.0 . .
K2 O9 H9A 110.6 . .
K1 O9 H9B 144.3 . .
K2 O9 H9B 88.2 . .
H9A O9 H9B 98.8 . .
K1 O10 K2 158.19(5) . 2_566
K1 O10 H10A 85.0 . .
K2 O10 H10A 88.6 2_566 .
K1 O10 H10B 112.5 . .
K2 O10 H10B 89.3 2_566 .
H10A O10 H10B 108.4 . .
H11A O11 H11B 107.3 . .
C7 C1 C6 111.24(14) . .
C7 C1 C2 115.11(16) . .
C6 C1 C2 108.51(14) . .
C7 C1 H1 107.2 . .
C6 C1 H1 107.2 . .
C2 C1 H1 107.2 . .
C8 C2 C3 114.44(15) . .
C8 C2 C1 112.58(14) . .
C3 C2 C1 108.75(15) . .
C8 C2 H2A 106.9 . .
C3 C2 H2A 106.9 . .
C1 C2 H2A 106.9 . .
C12 C3 C2 109.41(14) . .
C12 C3 C4 108.24(15) . .
C2 C3 C4 106.96(14) . .
C12 C3 H3 110.7 . .
C2 C3 H3 110.7 . .
C4 C3 H3 110.7 . .
C9 C4 C3 108.08(14) . .
C9 C4 C5 116.50(15) . .
C3 C4 C5 107.95(14) . .
C9 C4 H4 108.0 . .
C3 C4 H4 108.0 . .
C5 C4 H4 108.0 . .
C10 C5 C6 113.29(15) . .
C10 C5 C4 115.05(14) . .
C6 C5 C4 109.39(15) . .
C10 C5 H5 106.1 . .
C6 C5 H5 106.1 . .
C4 C5 H5 106.1 . .
C11 C6 C5 110.12(14) . .
C11 C6 C1 109.37(16) . .
C5 C6 C1 105.08(14) . .
C11 C6 H6 110.7 . .
C5 C6 H6 110.7 . .
C1 C6 H6 110.7 . .
O1 C7 O2 122.90(17) . .
O1 C7 C1 124.47(16) . .
O2 C7 C1 112.63(15) . .
O3 C8 O4 124.40(19) . .
O3 C8 C2 121.53(16) . .
O4 C8 C2 114.04(16) . .
O5 C9 O6 122.51(16) . .
O5 C9 C4 121.57(16) . .
O6 C9 C4 115.80(16) . .
O7 C10 O8 121.33(18) . .
O7 C10 C5 122.66(16) . .
O8 C10 C5 115.88(15) . .
C12 C11 C6 114.31(16) . .
C12 C11 H11 122.8 . .
C6 C11 H11 122.8 . .
C11 C12 C3 114.45(16) . .
C11 C12 H12 122.8 . .
C3 C12 H12 122.8 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
K1 O7 2.7471(13) 2
K1 O9 2.7863(15) .
K1 O3 2.7972(13) .
K1 O1 2.8314(14) .
K1 O10 2.8364(17) .
K1 O6 2.8903(13) 2_655
K1 O5 2.9791(13) 2_655
K1 C12 3.4504(19) .
K2 O5 2.6640(13) 2
K2 O4 2.7004(13) 2_556
K2 O9 2.8055(15) .
K2 O7 2.8095(13) 2
K2 O1 2.8976(13) .
K2 O3 2.9809(14) 1_455
K2 O10 3.0653(17) 2_566
K2 C10 3.4991(18) 2
O1 C7 1.222(2) .
O2 C7 1.306(2) .
O2 H2 0.9882 .
O3 C8 1.250(2) .
O3 K2 2.9810(14) 1_655
O4 C8 1.275(2) .
O4 K2 2.7004(13) 2_556
O5 C9 1.232(2) .
O5 K2 2.6640(13) 2
O5 K1 2.9791(13) 2_655
O6 C9 1.290(2) .
O6 K1 2.8903(13) 2_655
O7 C10 1.229(2) .
O7 K1 2.7471(13) 2
O7 K2 2.8095(13) 2
O8 C10 1.314(2) .
O8 H8 0.9944 .
O9 H9A 0.9204 .
O9 H9B 0.8304 .
O10 K2 3.0653(17) 2_566
O10 H10A 0.9223 .
O10 H10B 0.9203 .
O11 H11A 0.8692 .
O11 H11B 0.9035 .
C1 C7 1.520(3) .
C1 C6 1.549(3) .
C1 C2 1.577(2) .
C1 H1 0.9800 .
C2 C8 1.520(3) .
C2 C3 1.547(2) .
C2 H2A 0.9800 .
C3 C12 1.506(2) .
C3 C4 1.563(3) .
C3 H3 0.9800 .
C4 C9 1.534(2) .
C4 C5 1.567(2) .
C4 H4 0.9800 .
C5 C10 1.515(3) .
C5 C6 1.545(2) .
C5 H5 0.9800 .
C6 C11 1.504(2) .
C6 H6 0.9800 .
C11 C12 1.323(3) .
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
O2 H2 O4 0.99 1.49 2.4676(18) 169.7 2_556
O8 H8 O6 0.99 1.47 2.4608(17) 172.0 2_645
O9 H9A O2 0.92 1.94 2.8460(18) 167.5 2_556
O9 H9B O10 0.83 2.16 2.9013(19) 148.0 2_566
O10 H10A O11 0.92 1.92 2.8247(19) 168.1 .
O10 H10B O11 0.92 1.83 2.7339(19) 166.8 2_666
O11 H11A O3 0.87 1.97 2.778(2) 154.8 .
O11 H11B O8 0.90 1.95 2.8248(19) 163.2 1_566
