#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/44/2234481.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2234481
loop_
_publ_author_name
'Guo, Qing-Zhong'
'Du, Yi'
_publ_section_title
;
 5,7,13,15-Tetraoxo-2,2,10,10-tetrakis(trifluoromethyl)-4,8,12,16-tetraoxa-1(1,4),3(1,4),6(1,2),9(1,4),11(1,4),14(1,2)-hexabenzenahexadecaphane
 tetrahydrofuran monosolvate
;
_journal_coeditor_code           ZJ2060
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1126
_journal_paper_doi               10.1107/S1600536812011166
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C46 H24 F12 O8, C4 H8 O1'
_chemical_formula_moiety         'C46 H24 F12 O8, C4 H8 O1'
_chemical_formula_sum            'C50 H32 F12 O9'
_chemical_formula_weight         1004.76
_chemical_name_common
;
2,2,21,21-tetrakis(trifluoromethyl)-7,16,26,35-
tetraoxaheptacyclo[34.2.2.2^3,6^.2^17,20^.2^22,25^.0^9,14^.0^28,33^]
hexatetraconta-1(38),3,5,9,11,13,17,19,22,24,28(33),29,31,36,39,41,43,45-
octadecaene-8,15,27,34-tetrone tetrahydrofuran monosolvate
;
_chemical_name_systematic
;
5,7,13,15-Tetraoxo-2,2,10,10-tetrakis(trifluoromethyl)-4,8,12,16-
tetraoxa1-(1,4),3(1,4),6(1,2),9(1,4),11(1,4),14(1,2)-hexabenzenahexadecaphane
tetrahydrofuran monosolvate
;
_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                105.715(14)
_cell_angle_beta                 97.969(14)
_cell_angle_gamma                103.167(14)
_cell_formula_units_Z            1
_cell_length_a                   9.3857(17)
_cell_length_b                   11.2748(17)
_cell_length_c                   12.615(2)
_cell_measurement_reflns_used    23
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      20.143
_cell_measurement_theta_min      9.446
_cell_volume                     1222.3(4)
_computing_cell_refinement       'XSCANS (Bruker, 2001)'
_computing_data_collection       'XSCANS (Bruker, 2001)'
_computing_data_reduction        'XSCANS (Bruker, 2001)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device_type  'Siemens P4'
_diffrn_measurement_method       'ω scans'
_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  0.0217
_diffrn_reflns_av_sigmaI/netI    0.0923
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -1
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5660
_diffrn_reflns_theta_full        26.03
_diffrn_reflns_theta_max         26.03
_diffrn_reflns_theta_min         3.97
_diffrn_standards_decay_%        2.22
_diffrn_standards_interval_count 197
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.123
_exptl_absorpt_correction_T_max  0.9638
_exptl_absorpt_correction_T_min  0.9495
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(XSCANS; Bruker, 2001)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.319
_refine_diff_density_min         -0.198
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     344
_refine_ls_number_reflns         4684
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.1453
_refine_ls_R_factor_gt           0.0652
_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)+(0.0520P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1400
_refine_ls_wR_factor_ref         0.1577
_reflns_number_gt                1916
_reflns_number_total             4684
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            zj2060.cif
_cod_data_source_block           I
_cod_original_cell_volume        1222.4(3)
_cod_database_code               2234481
_cod_database_fobs_code          2234481
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
O O1 -0.0470(3) -0.3086(2) -0.5363(2) 0.0794(8) Uani d . 1 1
O O2 0.1569(4) -0.3494(4) -0.5872(3) 0.1347(15) Uani d . 1 1
O O3 0.8188(3) 0.3985(2) -0.1740(2) 0.0715(8) Uani d . 1 1
O O4 0.7764(4) 0.5631(3) -0.2264(3) 0.1049(11) Uani d . 1 1
F F1 0.1508(2) 0.2999(2) -0.0496(2) 0.1018(9) Uani d . 1 1
F F2 -0.0143(2) 0.1254(2) -0.1459(2) 0.0908(8) Uani d . 1 1
F F3 0.1038(3) 0.2448(2) -0.2304(2) 0.0860(7) Uani d . 1 1
F F4 0.3519(3) 0.2028(2) 0.04653(17) 0.1021(9) Uani d . 1 1
F F5 0.3492(3) 0.0118(3) -0.0450(2) 0.0933(8) Uani d . 1 1
F F6 0.1484(3) 0.0505(2) -0.00260(18) 0.0977(8) Uani d . 1 1
C C1 -0.0778(4) -0.4798(3) -0.7009(3) 0.0589(10) Uani d . 1 1
C C2 -0.2286(4) -0.5213(4) -0.7051(3) 0.0792(12) Uani d . 1 1
H H2 -0.2674 -0.4835 -0.6448 0.079 Uiso calc R 1 1
C C3 -0.3231(4) -0.6168(4) -0.7958(3) 0.0827(13) Uani d . 1 1
H H3 -0.4245 -0.6449 -0.7968 0.083 Uiso calc R 1 1
C C4 -0.2656(5) -0.6701(4) -0.8850(3) 0.0721(11) Uani d . 1 1
H H4 -0.3286 -0.7347 -0.9475 0.072 Uiso calc R 1 1
C C5 -0.1159(5) -0.6294(4) -0.8830(3) 0.0706(11) Uani d . 1 1
H H5 -0.0781 -0.6659 -0.9444 0.071 Uiso calc R 1 1
C C6 -0.0203(4) -0.5338(3) -0.7899(3) 0.0572(9) Uani d . 1 1
C C7 0.0240(5) -0.3755(4) -0.6024(3) 0.0736(11) Uani d . 1 1
C C8 0.0367(4) -0.2045(3) -0.4396(3) 0.0614(10) Uani d . 1 1
C C9 0.0224(4) -0.2157(3) -0.3377(4) 0.0724(11) Uani d . 1 1
H H9 -0.0326 -0.2923 -0.3313 0.072 Uiso calc R 1 1
C C10 0.0913(4) -0.1106(3) -0.2421(3) 0.0658(10) Uani d . 1 1
H H10 0.0832 -0.1175 -0.1712 0.066 Uiso calc R 1 1
C C11 0.1709(3) 0.0029(3) -0.2513(3) 0.0498(8) Uani d . 1 1
C C12 0.1826(4) 0.0095(3) -0.3588(3) 0.0617(10) Uani d . 1 1
H H12 0.2381 0.0852 -0.3665 0.062 Uiso calc R 1 1
C C13 0.1140(4) -0.0932(4) -0.4529(3) 0.0680(10) Uani d . 1 1
H H13 0.1198 -0.0874 -0.5244 0.068 Uiso calc R 1 1
C C14 0.2397(3) 0.1268(3) -0.1490(3) 0.0520(9) Uani d . 1 1
C C15 0.1194(4) 0.2006(4) -0.1444(4) 0.0738(12) Uani d . 1 1
C C16 0.2704(5) 0.0965(5) -0.0377(3) 0.0737(12) Uani d . 1 1
C C17 0.3893(4) 0.2048(3) -0.1606(3) 0.0495(8) Uani d . 1 1
C C18 0.4309(4) 0.3383(3) -0.1327(3) 0.0635(10) Uani d . 1 1
H H18 0.3630 0.3834 -0.1104 0.063 Uiso calc R 1 1
C C19 0.5725(4) 0.4043(3) -0.1380(3) 0.0640(10) Uani d . 1 1
H H19 0.5997 0.4934 -0.1176 0.064 Uiso calc R 1 1
C C20 0.6714(4) 0.3391(3) -0.1729(3) 0.0545(9) Uani d . 1 1
C C21 0.6330(4) 0.2069(3) -0.2027(3) 0.0603(10) Uani d . 1 1
H H21 0.7010 0.1625 -0.2264 0.060 Uiso calc R 1 1
C C22 0.4938(4) 0.1420(3) -0.1968(3) 0.0633(10) Uani d . 1 1
H H22 0.4681 0.0529 -0.2178 0.063 Uiso calc R 1 1
C C23 0.8577(5) 0.5007(4) -0.2080(3) 0.0692(11) Uani d . 1 1
O O5 0.6163(12) -0.0885(7) -0.3822(10) 0.172(4) Uani d P 0.50 1
C C24 0.5149(18) -0.1575(12) -0.4794(11) 0.152(5) Uani d P 0.50 1
H H24A 0.5250 -0.1136 -0.5355 0.152 Uiso calc PR 0.50 1
H H24B 0.4140 -0.1683 -0.4663 0.152 Uiso calc PR 0.50 1
C C25 0.5431(12) -0.2781(11) -0.5174(9) 0.123(4) Uani d P 0.50 1
H H25A 0.4539 -0.3425 -0.5655 0.123 Uiso calc PR 0.50 1
H H25B 0.6229 -0.2735 -0.5588 0.123 Uiso calc PR 0.50 1
C C26 0.5847(17) -0.3060(8) -0.4206(11) 0.140(5) Uani d P 0.50 1
H H26A 0.6684 -0.3428 -0.4242 0.140 Uiso calc PR 0.50 1
H H26B 0.5020 -0.3652 -0.4070 0.140 Uiso calc PR 0.50 1
C C27 0.632(2) -0.1677(12) -0.3238(8) 0.177(7) Uani d P 0.50 1
H H27A 0.5667 -0.1657 -0.2706 0.177 Uiso calc PR 0.50 1
H H27B 0.7349 -0.1466 -0.2832 0.177 Uiso calc PR 0.50 1
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'
F F 0.0171 0.0103 '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_site_symmetry_3
_geom_angle
C7 O1 C8 . 119.6(3)
C23 O3 C20 . 123.7(3)
C6 C1 C2 . 119.5(3)
C6 C1 C7 . 119.1(3)
C2 C1 C7 . 121.4(4)
C3 C2 C1 . 121.6(4)
C3 C2 H2 . 119.2
C1 C2 H2 . 119.2
C4 C3 C2 . 118.8(4)
C4 C3 H3 . 120.6
C2 C3 H3 . 120.6
C3 C4 C5 . 120.5(4)
C3 C4 H4 . 119.7
C5 C4 H4 . 119.7
C4 C5 C6 . 120.3(4)
C4 C5 H5 . 119.8
C6 C5 H5 . 119.8
C1 C6 C5 . 119.2(3)
C1 C6 C23 2_654 124.0(3)
C5 C6 C23 2_654 116.8(3)
O2 C7 O1 . 122.7(4)
O2 C7 C1 . 123.6(4)
O1 C7 C1 . 113.6(3)
C9 C8 C13 . 122.5(3)
C9 C8 O1 . 117.6(3)
C13 C8 O1 . 119.5(4)
C8 C9 C10 . 118.8(4)
C8 C9 H9 . 120.6
C10 C9 H9 . 120.6
C11 C10 C9 . 120.7(3)
C11 C10 H10 . 119.6
C9 C10 H10 . 119.6
C10 C11 C12 . 118.2(3)
C10 C11 C14 . 123.3(3)
C12 C11 C14 . 118.4(3)
C13 C12 C11 . 121.2(3)
C13 C12 H12 . 119.4
C11 C12 H12 . 119.4
C8 C13 C12 . 118.5(4)
C8 C13 H13 . 120.7
C12 C13 H13 . 120.7
C17 C14 C16 . 106.5(3)
C17 C14 C15 . 112.8(3)
C16 C14 C15 . 108.8(3)
C17 C14 C11 . 111.8(3)
C16 C14 C11 . 111.9(3)
C15 C14 C11 . 105.2(3)
F3 C15 F2 . 107.9(4)
F3 C15 F1 . 107.9(4)
F2 C15 F1 . 105.3(3)
F3 C15 C14 . 111.4(3)
F2 C15 C14 . 111.4(3)
F1 C15 C14 . 112.6(3)
F5 C16 F6 . 106.9(4)
F5 C16 F4 . 106.5(4)
F6 C16 F4 . 106.1(3)
F5 C16 C14 . 111.4(3)
F6 C16 C14 . 114.8(3)
F4 C16 C14 . 110.8(4)
C22 C17 C18 . 117.1(3)
C22 C17 C14 . 119.3(3)
C18 C17 C14 . 123.5(3)
C19 C18 C17 . 120.7(3)
C19 C18 H18 . 119.6
C17 C18 H18 . 119.6
C20 C19 C18 . 120.1(3)
C20 C19 H19 . 120.0
C18 C19 H19 . 120.0
C19 C20 C21 . 120.6(3)
C19 C20 O3 . 123.6(3)
C21 C20 O3 . 115.6(3)
C22 C21 C20 . 119.2(3)
C22 C21 H21 . 120.4
C20 C21 H21 . 120.4
C21 C22 C17 . 122.2(3)
C21 C22 H22 . 118.9
C17 C22 H22 . 118.9
O4 C23 O3 . 124.5(4)
O4 C23 C6 2_654 124.3(4)
O3 C23 C6 2_654 111.0(4)
C27 O5 C24 . 107.4(9)
O5 C24 C25 . 107.4(9)
O5 C24 H24A . 110.2
C25 C24 H24A . 110.2
O5 C24 H24B . 110.2
C25 C24 H24B . 110.2
H24A C24 H24B . 108.5
C26 C25 C24 . 104.2(9)
C26 C25 H25A . 110.9
C24 C25 H25A . 110.9
C26 C25 H25B . 110.9
C24 C25 H25B . 110.9
H25A C25 H25B . 108.9
C25 C26 C27 . 103.4(7)
C25 C26 H26A . 111.1
C27 C26 H26A . 111.1
C25 C26 H26B . 111.1
C27 C26 H26B . 111.1
H26A C26 H26B . 109.0
O5 C27 C26 . 102.8(7)
O5 C27 H27A . 111.2
C26 C27 H27A . 111.2
O5 C27 H27B . 111.2
C26 C27 H27B . 111.2
H27A C27 H27B . 109.1
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
O1 C7 . 1.324(4)
O1 C8 . 1.421(4)
O2 C7 . 1.190(4)
O3 C23 . 1.328(4)
O3 C20 . 1.397(4)
O4 C23 . 1.189(4)
F1 C15 . 1.341(4)
F2 C15 . 1.339(4)
F3 C15 . 1.314(5)
F4 C16 . 1.348(4)
F5 C16 . 1.326(5)
F6 C16 . 1.331(4)
C1 C6 . 1.367(5)
C1 C2 . 1.375(5)
C1 C7 . 1.486(5)
C2 C3 . 1.368(5)
C2 H2 . 0.9300
C3 C4 . 1.367(5)
C3 H3 . 0.9300
C4 C5 . 1.370(5)
C4 H4 . 0.9300
C5 C6 . 1.388(5)
C5 H5 . 0.9300
C6 C23 2_654 1.493(5)
C8 C9 . 1.348(5)
C8 C13 . 1.364(5)
C9 C10 . 1.391(5)
C9 H9 . 0.9300
C10 C11 . 1.370(4)
C10 H10 . 0.9300
C11 C12 . 1.396(5)
C11 C14 . 1.554(4)
C12 C13 . 1.368(5)
C12 H12 . 0.9300
C13 H13 . 0.9300
C14 C17 . 1.526(4)
C14 C16 . 1.538(5)
C14 C15 . 1.547(5)
C17 C22 . 1.393(5)
C17 C18 . 1.396(4)
C18 C19 . 1.387(5)
C18 H18 . 0.9300
C19 C20 . 1.359(5)
C19 H19 . 0.9300
C20 C21 . 1.381(4)
C21 C22 . 1.366(5)
C21 H21 . 0.9300
C22 H22 . 0.9300
C23 C6 2_654 1.493(5)
O5 C27 . 1.323(12)
O5 C24 . 1.355(12)
C24 C25 . 1.413(14)
C24 H24A . 0.9700
C24 H24B . 0.9700
C25 C26 . 1.369(13)
C25 H25A . 0.9700
C25 H25B . 0.9700
C26 C27 . 1.619(14)
C26 H26A . 0.9700
C26 H26B . 0.9700
C27 H27A . 0.9700
C27 H27B . 0.9700
