#------------------------------------------------------------------------------
#$Date: 2016-03-24 01:59:59 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179550 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/19/4501975.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_4501975
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 H13 Cs O9'
_chemical_formula_weight         434.13
_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                116.718(3)
_cell_angle_beta                 94.178(4)
_cell_angle_gamma                98.515(4)
_cell_formula_units_Z            2
_cell_length_a                   8.1702(3)
_cell_length_b                   9.6589(5)
_cell_length_c                   9.8979(5)
_cell_measurement_reflns_used    31743
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      25.68
_cell_measurement_theta_min      2.33
_cell_volume                     681.36(6)
_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 (617 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  0.0317
_diffrn_reflns_av_sigmaI/netI    0.0349
_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            31743
_diffrn_reflns_theta_full        25.68
_diffrn_reflns_theta_max         25.68
_diffrn_reflns_theta_min         2.33
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.765
_exptl_absorpt_correction_T_max  0.661
_exptl_absorpt_correction_T_min  0.535
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.116
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.414
_refine_diff_density_min         -0.812
_refine_diff_density_rms         0.093
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2575
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0232
_refine_ls_R_factor_gt           0.0207
_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)+(0.0284P)²+0.2521P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0517
_refine_ls_wR_factor_ref         0.0522
_reflns_number_gt                2472
_reflns_number_total             2575
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg100785r_si_002.cif
_cod_data_source_block           7
_cod_database_code               4501975
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
Cs Cs 0.764778(17) 0.450020(14) 0.187513(14) 0.02434(7) Uani 1 1 d .
O1 O 1.0616(2) 0.69651(19) 0.48095(18) 0.0222(3) Uani 1 1 d .
H1 H 1.1426 0.6402 0.4878 0.027 Uiso 1 1 d R
O2 O 1.0402(2) 0.74270(19) 0.72116(18) 0.0252(4) Uani 1 1 d .
O3 O 0.7309(2) 0.48208(17) 0.51112(17) 0.0210(3) Uani 1 1 d .
O4 O 0.6558(2) 0.57791(17) 0.74414(17) 0.0213(3) Uani 1 1 d .
O5 O 0.5312(2) 1.19448(19) 0.92761(18) 0.0241(4) Uani 1 1 d .
O6 O 0.3108(2) 1.08012(19) 0.74172(18) 0.0255(4) Uani 1 1 d .
H6 H 0.2558 1.1466 0.8128 0.031 Uiso 1 1 d R
O7 O 0.8789(2) 1.33322(17) 0.84114(17) 0.0208(3) Uani 1 1 d .
O8 O 0.6373(2) 1.29292(17) 0.69263(17) 0.0199(3) Uani 1 1 d .
H8 H 0.6660 1.4076 0.7192 0.024 Uiso 1 1 d R
O9 O 0.8019(2) 0.68885(18) 0.05016(18) 0.0239(3) Uani 1 1 d .
H9A H 0.7648 0.6580 -0.0525 0.029 Uiso 1 1 d R
H9B H 0.9206 0.6902 0.0648 0.029 Uiso 1 1 d R
C1 C 0.8417(3) 0.8213(2) 0.5904(2) 0.0174(4) Uani 1 1 d .
H1A H 0.8267 0.8113 0.4871 0.021 Uiso 1 1 calc R
C2 C 0.6736(3) 0.7389(2) 0.6128(2) 0.0171(4) Uani 1 1 d .
H2 H 0.5942 0.7038 0.5191 0.020 Uiso 1 1 calc R
C3 C 0.6018(3) 0.8631(2) 0.7439(2) 0.0170(4) Uani 1 1 d .
H3 H 0.5002 0.8130 0.7647 0.020 Uiso 1 1 calc R
C4 C 0.5609(3) 0.9826(2) 0.6858(2) 0.0166(4) Uani 1 1 d .
H4 H 0.4880 0.9234 0.5862 0.020 Uiso 1 1 calc R
C5 C 0.7302(3) 1.0654(2) 0.6647(2) 0.0161(4) Uani 1 1 d .
H5 H 0.7232 1.0326 0.5549 0.019 Uiso 1 1 calc R
C6 C 0.8758(3) 1.0008(2) 0.7073(2) 0.0171(4) Uani 1 1 d .
H6A H 0.9833 1.0555 0.7001 0.021 Uiso 1 1 calc R
C7 C 0.9905(3) 0.7497(2) 0.6065(2) 0.0188(4) Uani 1 1 d .
C8 C 0.6899(3) 0.5896(2) 0.6263(2) 0.0176(4) Uani 1 1 d .
C9 C 0.4695(3) 1.0976(2) 0.7978(2) 0.0177(4) Uani 1 1 d .
C10 C 0.7587(3) 1.2455(2) 0.7455(2) 0.0174(4) Uani 1 1 d .
C11 C 0.8738(3) 1.0202(2) 0.8667(2) 0.0184(4) Uani 1 1 d .
H11 H 0.9644 1.0769 0.9452 0.022 Uiso 1 1 calc R
C12 C 0.7318(3) 0.9496(2) 0.8857(2) 0.0201(5) Uani 1 1 d .
H12 H 0.7141 0.9532 0.9789 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'
Cs Cs -0.3680 2.1192 '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
O5 Cs O2 99.46(5) 1_544 2_766
O5 Cs O3 117.38(4) 1_544 .
O2 Cs O3 65.13(4) 2_766 .
O5 Cs O9 96.15(4) 1_544 .
O2 Cs O9 141.85(5) 2_766 .
O3 Cs O9 134.47(4) . .
O5 Cs O1 170.99(4) 1_544 .
O2 Cs O1 71.69(4) 2_766 .
O3 Cs O1 61.00(4) . .
O9 Cs O1 90.20(4) . .
O5 Cs O7 63.01(4) 1_544 1_544
O2 Cs O7 96.09(4) 2_766 1_544
O3 Cs O7 161.21(4) . 1_544
O9 Cs O7 61.03(4) . 1_544
O1 Cs O7 115.33(4) . 1_544
O5 Cs O7 124.81(4) 1_544 2_776
O2 Cs O7 92.52(4) 2_766 2_776
O3 Cs O7 116.53(4) . 2_776
O9 Cs O7 50.53(4) . 2_776
O1 Cs O7 55.57(4) . 2_776
O7 Cs O7 62.24(4) 1_544 2_776
O5 Cs O4 67.04(4) 1_544 2_666
O2 Cs O4 114.57(4) 2_766 2_666
O3 Cs O4 67.12(4) . 2_666
O9 Cs O4 103.57(4) . 2_666
O1 Cs O4 117.67(4) . 2_666
O7 Cs O4 124.58(4) 1_544 2_666
O7 Cs O4 149.29(3) 2_776 2_666
C7 O1 Cs 107.75(13) . .
C7 O1 H1 111.0 . .
Cs O1 H1 107.9 . .
C7 O2 Cs 139.06(14) . 2_766
C8 O3 Cs 131.00(13) . .
C8 O4 Cs 119.16(14) . 2_666
C9 O5 Cs 161.19(15) . 1_566
C9 O6 H6 112.2 . .
C10 O7 Cs 108.22(14) . 1_566
C10 O7 Cs 130.93(14) . 2_776
Cs O7 Cs 117.77(4) 1_566 2_776
C10 O8 H8 113.1 . .
Cs O9 H9A 122.6 . .
Cs O9 H9B 85.2 . .
H9A O9 H9B 109.6 . .
C7 C1 C6 110.53(18) . .
C7 C1 C2 113.81(17) . .
C6 C1 C2 108.40(17) . .
C7 C1 H1A 108.0 . .
C6 C1 H1A 108.0 . .
C2 C1 H1A 108.0 . .
Cs C1 H1A 48.8 . .
C8 C2 C3 115.58(17) . .
C8 C2 C1 112.60(17) . .
C3 C2 C1 109.23(17) . .
C8 C2 H2 106.3 . .
C3 C2 H2 106.3 . .
C1 C2 H2 106.3 . .
C12 C3 C2 110.12(18) . .
C12 C3 C4 109.13(17) . .
C2 C3 C4 105.26(16) . .
C12 C3 H3 110.7 . .
C2 C3 H3 110.7 . .
C4 C3 H3 110.7 . .
C9 C4 C3 109.35(16) . .
C9 C4 C5 113.16(17) . .
C3 C4 C5 107.81(17) . .
C9 C4 H4 108.8 . .
C3 C4 H4 108.8 . .
C5 C4 H4 108.8 . .
C10 C5 C6 113.60(18) . .
C10 C5 C4 113.71(17) . .
C6 C5 C4 109.63(16) . .
C10 C5 H5 106.4 . .
C6 C5 H5 106.4 . .
C4 C5 H5 106.4 . .
C11 C6 C5 109.29(18) . .
C11 C6 C1 109.54(17) . .
C5 C6 C1 105.85(17) . .
C11 C6 H6A 110.7 . .
C5 C6 H6A 110.7 . .
C1 C6 H6A 110.7 . .
O2 C7 O1 123.6(2) . .
O2 C7 C1 124.0(2) . .
O1 C7 C1 112.44(18) . .
O3 C8 O4 124.70(19) . .
O3 C8 C2 114.94(18) . .
O4 C8 C2 120.28(18) . .
O5 C9 O6 122.3(2) . .
O5 C9 C4 124.3(2) . .
O6 C9 C4 113.39(18) . .
O7 C10 O8 124.72(19) . .
O7 C10 C5 124.90(19) . .
O8 C10 C5 110.33(18) . .
C12 C11 C6 114.3(2) . .
C12 C11 H11 122.9 . .
C6 C11 H11 122.9 . .
C11 C12 C3 114.38(19) . .
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
Cs O5 2.9209(16) 1_544
Cs O2 3.0006(15) 2_766
Cs O3 3.1137(15) .
Cs O9 3.1520(16) .
Cs O1 3.3214(17) .
Cs O7 3.3459(16) 1_544
Cs O7 3.4335(16) 2_776
Cs O4 3.5447(17) 2_666
O1 C7 1.329(3) .
O1 H1 0.9337 .
O2 C7 1.211(3) .
O2 Cs 3.0006(15) 2_766
O3 C8 1.258(3) .
O4 C8 1.268(3) .
O4 Cs 3.5447(17) 2_666
O5 C9 1.211(3) .
O5 Cs 2.9209(16) 1_566
O6 C9 1.329(3) .
O6 H6 0.9135 .
O7 C10 1.215(3) .
O7 Cs 3.3458(16) 1_566
O7 Cs 3.4335(16) 2_776
O8 C10 1.319(3) .
O8 H8 1.0012 .
O9 H9A 0.9321 .
O9 H9B 0.9670 .
C1 C7 1.517(3) .
C1 C6 1.558(3) .
C1 C2 1.565(3) .
C1 H1A 0.9800 .
C2 C8 1.531(3) .
C2 C3 1.546(3) .
C2 H2 0.9800 .
C3 C12 1.503(3) .
C3 C4 1.567(3) .
C3 H3 0.9800 .
C4 C9 1.509(3) .
C4 C5 1.569(3) .
C4 H4 0.9800 .
C5 C10 1.523(3) .
C5 C6 1.538(3) .
C5 H5 0.9800 .
C6 C11 1.504(3) .
C6 H6A 0.9800 .
C11 C12 1.327(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
O1 H1 O3 0.93 1.68 2.612(2) 172.7 2_766
O6 H6 O9 0.91 1.72 2.612(2) 164.0 2_676
O8 H8 O4 1.00 1.57 2.542(2) 163.5 1_565
O9 H9A O4 0.93 1.89 2.815(2) 170.3 1_554
O9 H9B O7 0.97 1.92 2.822(2) 154.6 2_776
