#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/19/4501976.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_4501976
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 H19 Ba2 O13.5'
_chemical_formula_weight         653.95
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_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                 115.168(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.1150(4)
_cell_length_b                   14.8634(5)
_cell_length_c                   11.6445(3)
_cell_measurement_reflns_used    55076
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      25.68
_cell_measurement_theta_min      2.53
_cell_volume                     1741.12(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 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type
'Nonius Kappa-CCD area-detector diffractometer'
_diffrn_measurement_method
'two φ and four ω scans with 2° steps (420 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  0.0238
_diffrn_reflns_av_sigmaI/netI    0.0279
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            55076
_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    4.569
_exptl_absorpt_correction_T_max  0.578
_exptl_absorpt_correction_T_min  0.446
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.495
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             1244
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.722
_refine_diff_density_min         -1.089
_refine_diff_density_rms         0.177
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3305
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0265
_refine_ls_R_factor_gt           0.0229
_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)+(0.0360P)²+1.3821P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0574
_refine_ls_wR_factor_ref         0.0584
_reflns_number_gt                3086
_reflns_number_total             3305
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg100785r_si_002.cif
_cod_data_source_block           8
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_original_formula_sum        'C12 H19 Ba2 O13.50'
_cod_database_code               4501976
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, 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
Ba1 Ba 0.647356(17) 0.421771(11) 0.930561(16) 0.01853(7) Uani 1 1 d .
Ba2 Ba 0.472098(18) 0.146299(12) 0.797104(17) 0.01974(7) Uani 1 1 d .
O1 O 0.6248(2) 0.27759(14) 0.7555(2) 0.0227(5) Uani 1 1 d .
O2 O 0.7294(2) 0.39947(15) 0.7370(2) 0.0268(5) Uani 1 1 d .
O3 O 0.3583(2) 0.20323(15) 0.5481(2) 0.0248(5) Uani 1 1 d .
O4 O 0.3847(2) 0.35021(15) 0.5279(2) 0.0291(5) Uani 1 1 d .
O5 O 0.6239(2) -0.01013(14) 0.3816(2) 0.0228(5) Uani 1 1 d .
O6 O 0.6536(3) 0.05261(16) 0.2238(2) 0.0300(5) Uani 1 1 d .
O7 O 0.9097(2) 0.08252(14) 0.4959(2) 0.0268(5) Uani 1 1 d .
O8 O 0.9307(2) 0.19290(14) 0.3790(2) 0.0239(5) Uani 1 1 d .
O9 O 0.6868(2) 0.34932(15) 1.1752(2) 0.0269(5) Uani 1 1 d .
H9A H 0.6633 0.2933 1.1501 0.032 Uiso 1 1 d R
H9B H 0.6247 0.3785 1.1942 0.032 Uiso 1 1 d R
O10 O 0.4155(3) 0.4925(2) 0.7278(3) 0.0528(8) Uani 1 1 d .
H10A H 0.3336 0.4684 0.7016 0.063 Uiso 1 1 d R
H10B H 0.4248 0.4951 0.6546 0.063 Uiso 1 1 d R
O11 O 0.6897(2) 0.02916(15) 0.8790(2) 0.0275(5) Uani 1 1 d .
H11A H 0.7193 -0.0213 0.8437 0.033 Uiso 1 1 d R
H11B H 0.7667 0.0653 0.9169 0.033 Uiso 1 1 d R
O12 O 0.6516(2) 0.18307(16) 1.0627(2) 0.0287(5) Uani 1 1 d .
H12A H 0.7343 0.1781 1.0711 0.034 Uiso 1 1 d R
H12B H 0.6466 0.1504 1.1195 0.034 Uiso 1 1 d R
O13 O 0.4002(3) 0.09035(18) 0.9877(3) 0.0417(7) Uani 1 1 d .
H13A H 0.4684 0.0741 1.0483 0.050 Uiso 1 1 d R
H13B H 0.3391 0.0531 0.9674 0.050 Uiso 1 1 d R
O14 O 0.4932(10) 0.5148(6) 0.5611(8) 0.063(2) Uani 0.50 1 d P
C1 C 0.6590(3) 0.2947(2) 0.5646(3) 0.0186(6) Uani 1 1 d .
H1 H 0.6717 0.3476 0.5206 0.022 Uiso 1 1 calc R
C2 C 0.5227(3) 0.2511(2) 0.4773(3) 0.0188(6) Uani 1 1 d .
H2 H 0.4935 0.2812 0.3949 0.023 Uiso 1 1 calc R
C3 C 0.5414(3) 0.15070(19) 0.4529(3) 0.0190(6) Uani 1 1 d .
H3 H 0.4555 0.1203 0.4099 0.023 Uiso 1 1 calc R
C4 C 0.6181(3) 0.15190(19) 0.3685(3) 0.0179(6) Uani 1 1 d .
H4 H 0.5646 0.1871 0.2927 0.021 Uiso 1 1 calc R
C5 C 0.7521(3) 0.20428(19) 0.4406(3) 0.0179(6) Uani 1 1 d .
H5 H 0.7434 0.2622 0.3976 0.022 Uiso 1 1 calc R
C6 C 0.7696(3) 0.2246(2) 0.5786(3) 0.0190(6) Uani 1 1 d .
H6 H 0.8581 0.2493 0.6300 0.023 Uiso 1 1 calc R
C7 C 0.6712(3) 0.3254(2) 0.6949(3) 0.0200(6) Uani 1 1 d .
C8 C 0.4148(3) 0.2686(2) 0.5215(3) 0.0219(7) Uani 1 1 d .
C9 C 0.6341(3) 0.0582(2) 0.3233(3) 0.0205(6) Uani 1 1 d .
C10 C 0.8723(3) 0.15628(19) 0.4381(3) 0.0186(6) Uani 1 1 d .
C11 C 0.7458(3) 0.14115(19) 0.6391(3) 0.0199(6) Uani 1 1 d .
H11 H 0.8090 0.1175 0.7146 0.024 Uiso 1 1 calc R
C12 C 0.6274(3) 0.1043(2) 0.5758(3) 0.0198(6) Uani 1 1 d .
H12 H 0.5994 0.0538 0.6049 0.024 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'
Ba Ba -0.3244 2.2819 '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 Ba1 O5 71.60(7) 2_656 2_656
O7 Ba1 O2 124.24(7) 2_656 .
O5 Ba1 O2 100.21(7) 2_656 .
O7 Ba1 O8 108.05(7) 2_656 4_566
O5 Ba1 O8 144.68(6) 2_656 4_566
O2 Ba1 O8 107.57(6) . 4_566
O7 Ba1 O3 132.94(7) 2_656 4_666
O5 Ba1 O3 64.10(6) 2_656 4_666
O2 Ba1 O3 79.94(7) . 4_666
O8 Ba1 O3 99.40(6) 4_566 4_666
O7 Ba1 O10 71.67(9) 2_656 .
O5 Ba1 O10 136.67(8) 2_656 .
O2 Ba1 O10 82.27(8) . .
O8 Ba1 O10 69.83(7) 4_566 .
O3 Ba1 O10 155.23(8) 4_666 .
O7 Ba1 O1 156.35(7) 2_656 .
O5 Ba1 O1 127.39(6) 2_656 .
O2 Ba1 O1 45.77(6) . .
O8 Ba1 O1 65.76(6) 4_566 .
O3 Ba1 O1 70.24(6) 4_666 .
O10 Ba1 O1 85.00(8) . .
O7 Ba1 O9 88.56(7) 2_656 .
O5 Ba1 O9 69.68(6) 2_656 .
O2 Ba1 O9 141.78(7) . .
O8 Ba1 O9 75.00(7) 4_566 .
O3 Ba1 O9 62.32(7) 4_666 .
O10 Ba1 O9 130.97(8) . .
O1 Ba1 O9 110.41(6) . .
O7 Ba1 O7 66.06(7) 2_656 4_566
O5 Ba1 O7 114.62(6) 2_656 4_566
O2 Ba1 O7 144.74(7) . 4_566
O8 Ba1 O7 44.11(6) 4_566 4_566
O3 Ba1 O7 119.42(6) 4_666 4_566
O10 Ba1 O7 68.93(8) . 4_566
O1 Ba1 O7 109.64(6) . 4_566
O9 Ba1 O7 62.05(7) . 4_566
O8 Ba2 O3 91.67(7) 4_566 .
O8 Ba2 O1 69.17(6) 4_566 .
O3 Ba2 O1 68.90(6) . .
O8 Ba2 O5 147.96(7) 4_566 3_656
O3 Ba2 O5 64.94(6) . 3_656
O1 Ba2 O5 116.97(6) . 3_656
O8 Ba2 O13 80.33(7) 4_566 .
O3 Ba2 O13 140.39(8) . .
O1 Ba2 O13 139.16(7) . .
O5 Ba2 O13 103.36(8) 3_656 .
O8 Ba2 O11 133.38(7) 4_566 .
O3 Ba2 O11 119.53(6) . .
O1 Ba2 O11 89.58(7) . .
O5 Ba2 O11 78.61(7) 3_656 .
O13 Ba2 O11 92.40(7) . .
O8 Ba2 O9 80.51(7) 4_566 4_565
O3 Ba2 O9 63.70(7) . 4_565
O1 Ba2 O9 121.97(7) . 4_565
O5 Ba2 O9 69.74(6) 3_656 4_565
O13 Ba2 O9 76.71(8) . 4_565
O11 Ba2 O9 142.69(7) . 4_565
O8 Ba2 O12 66.54(7) 4_566 .
O3 Ba2 O12 148.66(7) . .
O1 Ba2 O12 81.95(6) . .
O5 Ba2 O12 143.17(6) 3_656 .
O13 Ba2 O12 60.82(8) . .
O11 Ba2 O12 69.79(7) . .
O9 Ba2 O12 129.06(6) 4_565 .
O8 Ba2 O6 134.96(6) 4_566 3_656
O3 Ba2 O6 102.19(6) . 3_656
O1 Ba2 O6 155.62(6) . 3_656
O5 Ba2 O6 42.26(6) 3_656 3_656
O13 Ba2 O6 61.72(7) . 3_656
O11 Ba2 O6 74.93(7) . 3_656
O9 Ba2 O6 68.46(6) 4_565 3_656
O12 Ba2 O6 109.15(6) . 3_656
C7 O1 Ba2 158.13(19) . .
C7 O1 Ba1 92.51(17) . .
Ba2 O1 Ba1 105.97(7) . .
C7 O2 Ba1 97.38(18) . .
C8 O3 Ba2 116.07(19) . .
C8 O3 Ba1 141.0(2) . 4_565
Ba2 O3 Ba1 102.78(7) . 4_565
C9 O5 Ba1 117.62(18) . 2_646
C9 O5 Ba2 106.21(18) . 3_656
Ba1 O5 Ba2 105.03(7) 2_646 3_656
C9 O6 Ba2 83.83(18) . 3_656
C10 O7 Ba1 150.4(2) . 2_646
C10 O7 Ba1 90.49(18) . 4_665
Ba1 O7 Ba1 113.95(7) 2_646 4_665
C10 O8 Ba2 142.08(19) . 4_665
C10 O8 Ba1 102.53(18) . 4_665
Ba2 O8 Ba1 110.86(7) 4_665 4_665
Ba2 O9 Ba1 98.68(7) 4_666 .
Ba2 O9 H9A 107.0 4_666 .
Ba1 O9 H9A 97.2 . .
Ba2 O9 H9B 130.9 4_666 .
Ba1 O9 H9B 104.3 . .
H9A O9 H9B 112.3 . .
Ba1 O10 H10A 124.0 . .
Ba1 O10 H10B 111.8 . .
H10A O10 H10B 101.7 . .
Ba2 O11 H11A 137.0 . .
Ba2 O11 H11B 106.6 . .
H11A O11 H11B 103.5 . .
Ba2 O12 H12A 108.0 . .
Ba2 O12 H12B 118.6 . .
H12A O12 H12B 106.1 . .
Ba2 O13 H13A 107.4 . .
Ba2 O13 H13B 116.7 . .
H13A O13 H13B 113.1 . .
C7 C1 C2 114.9(2) . .
C7 C1 C6 111.1(2) . .
C2 C1 C6 107.0(2) . .
C7 C1 H1 107.9 . .
C2 C1 H1 107.9 . .
C6 C1 H1 107.9 . .
C8 C2 C3 114.5(3) . .
C8 C2 C1 113.4(2) . .
C3 C2 C1 110.5(2) . .
C8 C2 H2 105.9 . .
C3 C2 H2 105.9 . .
C1 C2 H2 105.9 . .
C12 C3 C2 110.3(2) . .
C12 C3 C4 108.0(2) . .
C2 C3 C4 104.9(2) . .
C12 C3 H3 111.1 . .
C2 C3 H3 111.1 . .
C4 C3 H3 111.1 . .
C9 C4 C3 112.6(2) . .
C9 C4 C5 114.4(2) . .
C3 C4 C5 108.6(2) . .
C9 C4 H4 106.9 . .
C3 C4 H4 106.9 . .
C5 C4 H4 106.9 . .
C10 C5 C6 112.5(2) . .
C10 C5 C4 113.4(2) . .
C6 C5 C4 108.7(2) . .
C10 C5 H5 107.3 . .
C6 C5 H5 107.3 . .
C4 C5 H5 107.3 . .
C11 C6 C5 110.7(2) . .
C11 C6 C1 108.2(2) . .
C5 C6 C1 105.8(2) . .
C11 C6 H6 110.7 . .
C5 C6 H6 110.7 . .
C1 C6 H6 110.7 . .
O1 C7 O2 122.5(3) . .
O1 C7 C1 120.2(3) . .
O2 C7 C1 117.3(3) . .
O3 C8 O4 123.4(3) . .
O3 C8 C2 119.9(3) . .
O4 C8 C2 116.7(3) . .
O5 C9 O6 122.1(3) . .
O5 C9 C4 120.1(3) . .
O6 C9 C4 117.7(3) . .
O8 C10 O7 122.8(3) . .
O8 C10 C5 118.0(3) . .
O7 C10 C5 119.2(3) . .
C12 C11 C6 114.3(3) . .
C12 C11 H11 122.8 . .
C6 C11 H11 122.8 . .
C11 C12 C3 114.7(3) . .
C11 C12 H12 122.6 . .
C3 C12 H12 122.6 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ba1 O7 2.703(2) 2_656
Ba1 O5 2.746(2) 2_656
Ba1 O2 2.787(2) .
Ba1 O8 2.799(2) 4_566
Ba1 O3 2.845(2) 4_666
Ba1 O10 2.854(3) .
Ba1 O1 2.894(2) .
Ba1 O9 2.899(2) .
Ba1 O7 3.045(2) 4_566
Ba2 O8 2.685(2) 4_566
Ba2 O3 2.758(2) .
Ba2 O1 2.761(2) .
Ba2 O5 2.771(2) 3_656
Ba2 O13 2.786(3) .
Ba2 O11 2.798(2) .
Ba2 O9 2.872(2) 4_565
Ba2 O12 2.932(2) .
Ba2 O6 3.234(2) 3_656
O1 C7 1.257(4) .
O2 C7 1.265(4) .
O3 C8 1.265(4) .
O3 Ba1 2.845(2) 4_565
O4 C8 1.268(4) .
O5 C9 1.253(4) .
O5 Ba1 2.746(2) 2_646
O5 Ba2 2.771(2) 3_656
O6 C9 1.269(4) .
O6 Ba2 3.234(2) 3_656
O7 C10 1.261(4) .
O7 Ba1 2.703(2) 2_646
O7 Ba1 3.045(2) 4_665
O8 C10 1.253(4) .
O8 Ba2 2.685(2) 4_665
O8 Ba1 2.799(2) 4_665
O9 Ba2 2.872(2) 4_666
O9 H9A 0.8836 .
O9 H9B 0.9183 .
O10 H10A 0.9022 .
O10 H10B 0.9014 .
O11 H11A 0.9771 .
O11 H11B 0.9456 .
O12 H12A 0.8847 .
O12 H12B 0.8410 .
O13 H13A 0.8222 .
O13 H13B 0.8293 .
O14 O14 1.557(16) 3_666
C1 C7 1.533(4) .
C1 C2 1.562(4) .
C1 C6 1.566(4) .
C1 H1 0.9800 .
C2 C8 1.516(4) .
C2 C3 1.550(4) .
C2 H2 0.9800 .
C3 C12 1.508(4) .
C3 C4 1.551(4) .
C3 H3 0.9800 .
C4 C9 1.526(4) .
C4 C5 1.570(4) .
C4 H4 0.9800 .
C5 C10 1.526(4) .
C5 C6 1.564(4) .
C5 H5 0.9800 .
C6 C11 1.504(4) .
C6 H6 0.9800 .
C11 C12 1.323(4) .
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
O9 H9A O12 0.88 1.90 2.746(3) 158.5 .
O9 H9B O10 0.92 2.25 3.031(4) 143.2 3_667
O10 H10A O6 0.90 2.15 2.969(4) 151.1 4_566
O10 H10B O14 0.90 1.60 2.459(9) 158.6 .
O11 H11A O2 0.98 1.75 2.717(3) 171.6 2_646
O11 H11B O4 0.95 1.88 2.779(3) 158.4 4_666
O12 H12A O4 0.88 1.99 2.831(3) 159.5 4_666
O12 H12B O6 0.84 1.87 2.691(3) 163.5 1_556
O13 H13A O6 0.82 2.22 3.036(4) 170.7 1_556
O13 H13B O11 0.83 2.30 2.808(3) 120.1 3_657
