#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/18/7051861.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_7051861
loop_
_publ_author_name
'le Roex, Tanya'
'Nassimbeni, Luigi R.'
'Weber, Edwin'
_publ_section_title
;
 Selectivity and structure of mixed guest clathrates
;
_journal_issue                   5
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              856
_journal_paper_doi               10.1039/b718397f
_journal_volume                  32
_journal_year                    2008
_chemical_formula_moiety         'C28 H18 O2. 2(C2 H6 O)'
_chemical_formula_sum            'C32 H30 O4'
_chemical_formula_weight         478.56
_chemical_name_common            none
_chemical_name_systematic
;
9,9'-(ethyne-1,2-diyl)difluoren-9-ol). 2(ethanol)
clathrate

;
_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                 91.77(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.755(2)
_cell_length_b                   10.638(2)
_cell_length_c                   24.811(5)
_cell_measurement_reflns_used    19295
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      24.41
_cell_measurement_theta_min      1.02
_cell_volume                     2573.5(9)
_computing_cell_refinement       'Collect (Nonius, 2000)'
_computing_data_collection       'Collect (Nonius, 2000)'
_computing_data_reduction        'Collect (Nonius, 2000)'
_computing_molecular_graphics    'XSEED, a graphical interface to SHELX(1999)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       'combination of phi and omega'
_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  0.0713
_diffrn_reflns_av_sigmaI/netI    0.1012
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            7587
_diffrn_reflns_theta_full        24.47
_diffrn_reflns_theta_max         24.47
_diffrn_reflns_theta_min         2.52
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.235
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    .
_exptl_crystal_description       'clear plates'
_exptl_crystal_F_000             1016
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.381
_refine_diff_density_min         -0.419
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     345
_refine_ls_number_reflns         4220
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.1596
_refine_ls_R_factor_gt           0.0762
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0966P)²+0.9023P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1885
_refine_ls_wR_factor_ref         0.2210
_reflns_number_gt                2123
_reflns_number_total             4220
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b718397f.txt
_cod_data_source_block           c:\H2.2EtOH
_cod_original_sg_symbol_H-M      P21/n
_cod_database_code               7051861
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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.8476(4) 0.1557(6) 0.10050(16) 0.0822(19) Uani 1 1 d . . .
H1 H 0.9061 0.2169 0.1170 0.099 Uiso 1 1 calc R . .
C2 C 0.8953(5) 0.0766(7) 0.06056(19) 0.097(2) Uani 1 1 d . . .
H2 H 0.9876 0.0833 0.0498 0.116 Uiso 1 1 calc R . .
C3 C 0.8083(6) -0.0130(6) 0.03595(18) 0.091(2) Uani 1 1 d . . .
H3 H 0.8421 -0.0665 0.0087 0.109 Uiso 1 1 calc R . .
C4 C 0.6763(5) -0.0237(5) 0.05076(15) 0.0767(16) Uani 1 1 d . . .
H4 H 0.6177 -0.0841 0.0338 0.092 Uiso 1 1 calc R . .
C5 C 0.3710(4) -0.0020(5) 0.10335(15) 0.0653(15) Uani 1 1 d . . .
H5 H 0.3669 -0.0655 0.0764 0.078 Uiso 1 1 calc R . .
C6 C 0.2558(4) 0.0272(5) 0.13163(17) 0.0685(15) Uani 1 1 d . . .
H6 H 0.1731 -0.0178 0.1246 0.082 Uiso 1 1 calc R . .
C7 C 0.2595(4) 0.1214(5) 0.17014(16) 0.0711(16) Uani 1 1 d . . .
H7 H 0.1791 0.1415 0.1890 0.085 Uiso 1 1 calc R . .
C8 C 0.3799(4) 0.1866(4) 0.18131(15) 0.0614(15) Uani 1 1 d . . .
H8 H 0.3829 0.2508 0.2079 0.074 Uiso 1 1 calc R . .
O9 O 0.6935(3) 0.1919(3) 0.21111(9) 0.0664(13) Uani 1 1 d D . .
C9 C 0.6368(4) 0.2160(5) 0.15789(13) 0.0584(15) Uani 1 1 d . . .
H9 H 0.7842(19) 0.215(5) 0.213(2) 0.12(2) Uiso 1 1 d D . .
C10 C 0.6311(4) 0.3500(6) 0.14617(14) 0.0567(15) Uani 1 1 d . . .
C11 C 0.6218(4) 0.4584(6) 0.13343(14) 0.0585(16) Uani 1 1 d . . .
O12 O 0.6536(3) 0.6755(3) 0.15699(9) 0.0684(13) Uani 1 1 d D . .
C12 C 0.6056(4) 0.5909(5) 0.11594(13) 0.0569(15) Uani 1 1 d . . .
H12 H 0.7515(12) 0.680(4) 0.1614(16) 0.082(14) Uiso 1 1 d D . .
C13 C 0.3459(4) 0.6249(5) 0.13452(15) 0.0735(17) Uani 1 1 d . . .
H13 H 0.3564 0.6024 0.1715 0.088 Uiso 1 1 calc R . .
C14 C 0.2197(4) 0.6602(5) 0.11338(17) 0.0751(17) Uani 1 1 d . . .
H14 H 0.1422 0.6610 0.1357 0.090 Uiso 1 1 calc R . .
C15 C 0.2053(4) 0.6946(5) 0.05946(17) 0.0743(17) Uani 1 1 d . . .
H15 H 0.1181 0.7203 0.0454 0.089 Uiso 1 1 calc R . .
C16 C 0.3154(4) 0.6918(4) 0.02628(15) 0.0670(16) Uani 1 1 d . . .
H16 H 0.3041 0.7134 -0.0107 0.080 Uiso 1 1 calc R . .
C17 C 0.6176(4) 0.6715(4) -0.02955(14) 0.0615(15) Uani 1 1 d . . .
H17 H 0.5521 0.6953 -0.0568 0.074 Uiso 1 1 calc R . .
C18 C 0.7545(4) 0.6589(4) -0.04147(14) 0.0640(15) Uani 1 1 d . . .
H18 H 0.7832 0.6743 -0.0771 0.077 Uiso 1 1 calc R . .
C19 C 0.8496(4) 0.6240(5) -0.00204(14) 0.0636(15) Uani 1 1 d . . .
H19 H 0.9434 0.6161 -0.0107 0.076 Uiso 1 1 calc R . .
C20 C 0.8094(4) 0.6004(4) 0.05021(13) 0.0612(15) Uani 1 1 d . . .
H20 H 0.8752 0.5765 0.0773 0.073 Uiso 1 1 calc R . .
C1A C 0.7135(4) 0.1433(5) 0.11562(13) 0.0656(16) Uani 1 1 d . . .
C4A C 0.6271(4) 0.0536(5) 0.09071(14) 0.0652(15) Uani 1 1 d . . .
C5A C 0.4915(4) 0.0608(4) 0.11408(14) 0.0610(15) Uani 1 1 d . . .
C8A C 0.4954(4) 0.1569(4) 0.15314(13) 0.0590(15) Uani 1 1 d . . .
C13A C 0.4565(4) 0.6227(5) 0.10160(13) 0.0595(14) Uani 1 1 d . . .
C16A C 0.4424(4) 0.6575(4) 0.04719(13) 0.0584(15) Uani 1 1 d . . .
C17A C 0.5768(4) 0.6488(4) 0.02300(13) 0.0591(15) Uani 1 1 d . . .
C20A C 0.6743(4) 0.6120(4) 0.06227(13) 0.0567(14) Uani 1 1 d . . .
O1G O 0.9506(3) 0.2481(4) 0.24674(11) 0.0780(13) Uani 1 1 d D . .
C1G C 0.9922(6) 0.3767(6) 0.2530(2) 0.110(2) Uani 1 1 d . . .
H1GA H 0.9110 0.4283 0.2613 0.132 Uiso 1 1 calc R . .
H1GB H 1.0583 0.3832 0.2840 0.132 Uiso 1 1 calc R . .
C2G C 1.0534(8) 0.4254(6) 0.2065(2) 0.140(3) Uani 1 1 d . . .
H2GA H 1.1352 0.3761 0.1986 0.210 Uiso 1 1 calc R . .
H2GB H 1.0795 0.5133 0.2128 0.210 Uiso 1 1 calc R . .
H2GC H 0.9879 0.4206 0.1758 0.210 Uiso 1 1 calc R . .
O3G O 0.9117(3) 0.7167(4) 0.18885(11) 0.0715(13) Uani 1 1 d D . .
C3G C 0.9206(8) 0.8492(8) 0.1766(2) 0.149(3) Uani 1 1 d D . .
H3GA H 0.9825 0.8556 0.1458 0.179 Uiso 1 1 calc R . .
H3GB H 0.8284 0.8737 0.1625 0.179 Uiso 1 1 calc R . .
C4G C 0.9606(9) 0.9425(6) 0.2117(2) 0.144(3) Uani 1 1 d D . .
H4GA H 0.9119 0.9330 0.2455 0.215 Uiso 1 1 calc R . .
H4GB H 0.9388 1.0246 0.1957 0.215 Uiso 1 1 calc R . .
H4GC H 1.0596 0.9366 0.2192 0.215 Uiso 1 1 calc R . .
H3G H 0.877(9) 0.702(9) 0.2241(16) 0.25(4) Uiso 1 1 d D . .
H1G H 0.913(6) 0.225(6) 0.2808(13) 0.16(3) Uiso 1 1 d D . .
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'
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
_geom_angle_publ_flag
C1A C1 C2 118.5(5) . . ?
C1 C2 C3 120.7(5) . . ?
C4 C3 C2 120.4(5) . . ?
C3 C4 C4A 119.8(5) . . ?
C5A C5 C6 119.9(4) . . ?
C5 C6 C7 120.6(4) . . ?
C8 C7 C6 120.3(4) . . ?
C8A C8 C7 119.0(4) . . ?
O9 C9 C10 111.6(4) . . ?
O9 C9 C8A 108.7(3) . . ?
C10 C9 C8A 111.2(3) . . ?
O9 C9 C1A 111.1(3) . . ?
C10 C9 C1A 112.2(3) . . ?
C8A C9 C1A 101.6(4) . . ?
C11 C10 C9 175.7(4) . . ?
C10 C11 C12 177.5(4) . . ?
O12 C12 C11 111.2(3) . . ?
O12 C12 C13A 108.4(3) . . ?
C11 C12 C13A 111.8(3) . . ?
O12 C12 C20A 112.8(3) . . ?
C11 C12 C20A 110.5(4) . . ?
C13A C12 C20A 101.8(3) . . ?
C13A C13 C14 119.2(4) . . ?
C13 C14 C15 120.1(4) . . ?
C16 C15 C14 120.9(4) . . ?
C15 C16 C16A 119.4(4) . . ?
C18 C17 C17A 119.2(3) . . ?
C19 C18 C17 120.5(3) . . ?
C18 C19 C20 120.5(4) . . ?
C20A C20 C19 119.4(3) . . ?
C1 C1A C4A 120.5(4) . . ?
C1 C1A C9 129.1(4) . . ?
C4A C1A C9 110.4(3) . . ?
C4 C4A C1A 120.1(4) . . ?
C4 C4A C5A 130.7(4) . . ?
C1A C4A C5A 109.1(4) . . ?
C5 C5A C8A 119.5(4) . . ?
C5 C5A C4A 132.7(4) . . ?
C8A C5A C4A 107.8(4) . . ?
C8 C8A C5A 120.6(4) . . ?
C8 C8A C9 128.3(4) . . ?
C5A C8A C9 111.1(3) . . ?
C13 C13A C16A 120.8(4) . . ?
C13 C13A C12 128.8(3) . . ?
C16A C13A C12 110.3(3) . . ?
C16 C16A C13A 119.5(4) . . ?
C16 C16A C17A 132.1(3) . . ?
C13A C16A C17A 108.4(3) . . ?
C17 C17A C20A 119.5(4) . . ?
C17 C17A C16A 131.1(3) . . ?
C20A C17A C16A 109.4(3) . . ?
C20 C20A C17A 120.9(3) . . ?
C20 C20A C12 129.1(3) . . ?
C17A C20A C12 110.0(3) . . ?
C2G C1G O1G 112.7(4) . . ?
C4G C3G O3G 126.2(5) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C1A 1.378(6) . ?
C1 C2 1.391(7) . ?
C2 C3 1.403(7) . ?
C3 C4 1.354(7) . ?
C4 C4A 1.385(6) . ?
C5 C5A 1.371(6) . ?
C5 C6 1.378(6) . ?
C6 C7 1.385(6) . ?
C7 C8 1.384(6) . ?
C8 C8A 1.381(5) . ?
O9 C9 1.439(4) . ?
C9 C10 1.456(7) . ?
C9 C8A 1.517(5) . ?
C9 C1A 1.519(6) . ?
C10 C11 1.199(7) . ?
C11 C12 1.482(7) . ?
O12 C12 1.427(4) . ?
C12 C13A 1.525(5) . ?
C12 C20A 1.525(5) . ?
C13 C13A 1.374(5) . ?
C13 C14 1.375(6) . ?
C14 C15 1.390(6) . ?
C15 C16 1.374(6) . ?
C16 C16A 1.377(5) . ?
C17 C18 1.384(5) . ?
C17 C17A 1.396(5) . ?
C18 C19 1.378(5) . ?
C19 C20 1.389(5) . ?
C20 C20A 1.366(5) . ?
C1A C4A 1.404(6) . ?
C4A C5A 1.463(6) . ?
C5A C8A 1.408(6) . ?
C13A C16A 1.402(5) . ?
C16A C17A 1.461(5) . ?
C17A C20A 1.396(5) . ?
O1G C1G 1.434(6) . ?
C1G C2G 1.415(7) . ?
O3G C3G 1.446(8) . ?
C3G C4G 1.370(4) . ?
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 H9 O1G 0.917(10) 1.84(2) 2.700(4) 156(5) .
O12 H12 O3G 0.959(10) 1.731(18) 2.652(4) 160(4) .
O1G H1G O12 0.963(10) 1.774(12) 2.736(4) 178(6) 2_645
O3G H3G O9 0.961(10) 1.771(15) 2.728(4) 173(9) 2_655
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1A C1 C2 C3 0.6(7) . . . . ?
C1 C2 C3 C4 0.0(7) . . . . ?
C2 C3 C4 C4A -0.4(7) . . . . ?
C5A C5 C6 C7 1.4(6) . . . . ?
C5 C6 C7 C8 -0.9(6) . . . . ?
C6 C7 C8 C8A 0.6(6) . . . . ?
C13A C13 C14 C15 -0.8(7) . . . . ?
C13 C14 C15 C16 1.2(7) . . . . ?
C14 C15 C16 C16A -1.6(7) . . . . ?
C17A C17 C18 C19 0.2(6) . . . . ?
C17 C18 C19 C20 0.3(7) . . . . ?
C18 C19 C20 C20A 0.0(7) . . . . ?
C2 C1 C1A C4A -0.7(6) . . . . ?
C2 C1 C1A C9 179.5(4) . . . . ?
O9 C9 C1A C1 -65.4(6) . . . . ?
C10 C9 C1A C1 60.3(5) . . . . ?
C8A C9 C1A C1 179.1(4) . . . . ?
O9 C9 C1A C4A 114.8(4) . . . . ?
C10 C9 C1A C4A -119.5(4) . . . . ?
C8A C9 C1A C4A -0.7(4) . . . . ?
C3 C4 C4A C1A 0.3(6) . . . . ?
C3 C4 C4A C5A -179.6(4) . . . . ?
C1 C1A C4A C4 0.3(6) . . . . ?
C9 C1A C4A C4 -179.9(4) . . . . ?
C1 C1A C4A C5A -179.8(4) . . . . ?
C9 C1A C4A C5A 0.1(5) . . . . ?
C6 C5 C5A C8A -1.5(6) . . . . ?
C6 C5 C5A C4A -178.4(4) . . . . ?
C4 C4A C5A C5 -2.3(7) . . . . ?
C1A C4A C5A C5 177.8(4) . . . . ?
C4 C4A C5A C8A -179.4(4) . . . . ?
C1A C4A C5A C8A 0.7(4) . . . . ?
C7 C8 C8A C5A -0.7(6) . . . . ?
C7 C8 C8A C9 179.2(4) . . . . ?
C5 C5A C8A C8 1.2(6) . . . . ?
C4A C5A C8A C8 178.8(4) . . . . ?
C5 C5A C8A C9 -178.7(4) . . . . ?
C4A C5A C8A C9 -1.1(4) . . . . ?
O9 C9 C8A C8 64.0(6) . . . . ?
C10 C9 C8A C8 -59.3(5) . . . . ?
C1A C9 C8A C8 -178.8(4) . . . . ?
O9 C9 C8A C5A -116.1(4) . . . . ?
C10 C9 C8A C5A 120.6(4) . . . . ?
C1A C9 C8A C5A 1.1(4) . . . . ?
C14 C13 C13A C16A 0.9(7) . . . . ?
C14 C13 C13A C12 178.1(5) . . . . ?
O12 C12 C13A C13 -58.5(6) . . . . ?
C11 C12 C13A C13 64.4(6) . . . . ?
C20A C12 C13A C13 -177.6(5) . . . . ?
O12 C12 C13A C16A 119.0(4) . . . . ?
C11 C12 C13A C16A -118.1(4) . . . . ?
C20A C12 C13A C16A -0.1(5) . . . . ?
C15 C16 C16A C13A 1.7(7) . . . . ?
C15 C16 C16A C17A -178.3(4) . . . . ?
C13 C13A C16A C16 -1.3(7) . . . . ?
C12 C13A C16A C16 -179.0(4) . . . . ?
C13 C13A C16A C17A 178.7(4) . . . . ?
C12 C13A C16A C17A 1.0(5) . . . . ?
C18 C17 C17A C20A -1.0(6) . . . . ?
C18 C17 C17A C16A 178.3(4) . . . . ?
C16 C16A C17A C17 -0.9(8) . . . . ?
C13A C16A C17A C17 179.2(5) . . . . ?
C16 C16A C17A C20A 178.5(5) . . . . ?
C13A C16A C17A C20A -1.5(5) . . . . ?
C19 C20 C20A C17A -0.9(7) . . . . ?
C19 C20 C20A C12 179.8(5) . . . . ?
C17 C17A C20A C20 1.4(7) . . . . ?
C16A C17A C20A C20 -178.1(4) . . . . ?
C17 C17A C20A C12 -179.2(4) . . . . ?
C16A C17A C20A C12 1.4(5) . . . . ?
O12 C12 C20A C20 62.7(6) . . . . ?
C11 C12 C20A C20 -62.4(5) . . . . ?
C13A C12 C20A C20 178.7(4) . . . . ?
O12 C12 C20A C17A -116.8(4) . . . . ?
C11 C12 C20A C17A 118.2(4) . . . . ?
C13A C12 C20A C17A -0.8(5) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21117797
