#------------------------------------------------------------------------------
#$Date: 2016-03-21 08:01:09 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178590 $
#$URL: svn://www.crystallography.net/cod/cif/4/07/01/4070140.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_4070140
loop_
_publ_author_name
'Tikhonova, Irina A.'
'Gribanyov, Dmitry A.'
'Tugashov, Kirill I.'
'Dolgushin, Fedor M.'
'Smol’yakov, Alexandr F.'
'Peregudov, Alexandr S.'
'Klemenkova, Zinaida S.'
'Shur, Vladimir B.'
_publ_section_title
;
 Complexation of [12]Crown-4, [18]Crown-6, and 1,3,5-Trioxane with Cyclic
 Trimeric Perfluoro-o-phenylenemercury. Synthesis and Structures of the
 First Complexes of Crown Ethers with an Anticrown
;
_journal_issue                   22
_journal_name_full               Organometallics
_journal_page_first              6567
_journal_paper_doi               10.1021/om900626j
_journal_volume                  28
_journal_year                    2009
_chemical_formula_moiety         'C12 H24 O6, 2(C18 H2 F12 Hg3 O)'
_chemical_formula_sum            'C48 H28 F24 Hg6 O8'
_chemical_formula_weight         2392.24
_chemical_name_systematic
; 
 ? 
;
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                112.9600(10)
_cell_angle_beta                 98.0810(10)
_cell_angle_gamma                109.0410(10)
_cell_formula_units_Z            1
_cell_length_a                   11.6411(7)
_cell_length_b                   11.7927(7)
_cell_length_c                   11.8557(7)
_cell_measurement_reflns_used    693
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      32
_cell_measurement_theta_min      3
_cell_volume                     1347.88(14)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX II'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX II CCD area detector''
_diffrn_measurement_method       'omega 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  0.0370
_diffrn_reflns_av_sigmaI/netI    0.0340
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            33399
_diffrn_reflns_theta_full        32.00
_diffrn_reflns_theta_max         32.00
_diffrn_reflns_theta_min         1.95
_exptl_absorpt_coefficient_mu    17.158
_exptl_absorpt_correction_T_max  0.170
_exptl_absorpt_correction_T_min  0.079
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.947
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1076
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.16
_refine_diff_density_max         1.430
_refine_diff_density_min         -1.440
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     396
_refine_ls_number_reflns         9338
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.005
_refine_ls_R_factor_all          0.0308
_refine_ls_R_factor_gt           0.0235
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0185P)²+1.8843P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0474
_refine_ls_wR_factor_ref         0.0495
_reflns_number_gt                8194
_reflns_number_total             9338
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            om900626j_si_001.cif
_cod_data_source_block           aa
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               4070140
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
Hg1 Hg 0.668989(12) 0.615604(13) 0.884538(12) 0.01290(3) Uani 1 1 d .
Hg2 Hg 0.997541(12) 0.852473(12) 1.026120(12) 0.01243(3) Uani 1 1 d .
Hg3 Hg 0.878358(12) 0.623007(13) 0.686035(12) 0.01268(3) Uani 1 1 d .
F3 F 1.0372(2) 1.0332(2) 1.3216(2) 0.0220(5) Uani 1 1 d .
F4 F 0.8772(3) 1.0327(2) 1.4660(2) 0.0261(5) Uani 1 1 d .
F5 F 0.6275(2) 0.8545(2) 1.3578(2) 0.0252(5) Uani 1 1 d .
F6 F 0.5394(2) 0.6680(2) 1.1064(2) 0.0216(5) Uani 1 1 d .
F9 F 1.1073(2) 0.6922(2) 0.5732(2) 0.0230(5) Uani 1 1 d .
F10 F 1.3509(2) 0.8849(3) 0.6816(2) 0.0250(5) Uani 1 1 d .
F11 F 1.4362(2) 1.0637(2) 0.9362(2) 0.0242(5) Uani 1 1 d .
F12 F 1.2785(2) 1.0521(2) 1.0819(2) 0.0247(5) Uani 1 1 d .
F15 F 0.3925(2) 0.4071(2) 0.6956(2) 0.0234(5) Uani 1 1 d .
F16 F 0.3006(2) 0.2409(3) 0.4396(2) 0.0288(6) Uani 1 1 d .
F17 F 0.4602(2) 0.2445(3) 0.2926(2) 0.0282(6) Uani 1 1 d .
F18 F 0.7091(2) 0.4124(2) 0.4007(2) 0.0231(5) Uani 1 1 d .
O1W O 0.8919(3) 0.5730(3) 0.9263(3) 0.0146(5) Uani 1 1 d .
H1W H 0.890(6) 0.553(6) 0.980(6) 0.049(19) Uiso 1 1 d .
H2W H 0.928(6) 0.530(7) 0.886(6) 0.06(2) Uiso 1 1 d .
O1 O 0.9116(3) 0.3723(3) 0.7216(2) 0.0163(5) Uani 1 1 d .
O2 O 1.1638(3) 0.5360(3) 0.9029(2) 0.0163(5) Uani 1 1 d .
O3 O 1.2012(3) 0.7661(3) 1.1376(2) 0.0170(5) Uani 1 1 d .
C1 C 0.7433(4) 0.7500(4) 1.0788(3) 0.0160(7) Uani 1 1 d .
C2 C 0.8731(3) 0.8461(3) 1.1350(3) 0.0134(6) Uani 1 1 d .
C3 C 0.9143(4) 0.9392(4) 1.2648(3) 0.0165(7) Uani 1 1 d .
C4 C 0.8338(4) 0.9405(4) 1.3401(3) 0.0183(7) Uani 1 1 d .
C5 C 0.7071(4) 0.8496(4) 1.2864(4) 0.0194(7) Uani 1 1 d .
C6 C 0.6640(3) 0.7554(4) 1.1567(4) 0.0163(7) Uani 1 1 d .
C7 C 1.1097(3) 0.8603(3) 0.9053(3) 0.0126(6) Uani 1 1 d .
C8 C 1.0652(3) 0.7670(4) 0.7726(3) 0.0137(6) Uani 1 1 d .
C9 C 1.1475(4) 0.7781(4) 0.7009(3) 0.0153(7) Uani 1 1 d .
C10 C 1.2729(4) 0.8755(4) 0.7544(4) 0.0177(7) Uani 1 1 d .
C11 C 1.3165(3) 0.9672(4) 0.8835(4) 0.0176(7) Uani 1 1 d .
C12 C 1.2336(4) 0.9589(4) 0.9561(3) 0.0169(7) Uani 1 1 d .
C13 C 0.6863(3) 0.4928(3) 0.6102(3) 0.0151(6) Uani 1 1 d .
C14 C 0.6036(3) 0.4909(4) 0.6874(3) 0.0139(6) Uani 1 1 d .
C15 C 0.4759(3) 0.4074(4) 0.6268(4) 0.0162(7) Uani 1 1 d .
C16 C 0.4268(3) 0.3217(4) 0.4949(4) 0.0182(7) Uani 1 1 d .
C17 C 0.5073(4) 0.3237(4) 0.4207(3) 0.0194(7) Uani 1 1 d .
C18 C 0.6347(4) 0.4097(4) 0.4787(3) 0.0165(7) Uani 1 1 d .
C19 C 0.7905(4) 0.2573(4) 0.6635(3) 0.0170(7) Uani 1 1 d .
H19A H 0.7801 0.2038 0.5715 0.020 Uiso 1 1 calc R
H19B H 0.7219 0.2895 0.6680 0.020 Uiso 1 1 calc R
C20 C 1.0177(4) 0.3387(4) 0.7090(4) 0.0192(7) Uani 1 1 d .
H20A H 1.0065 0.2839 0.6169 0.023 Uiso 1 1 calc R
H20B H 1.0238 0.2846 0.7540 0.023 Uiso 1 1 calc R
C21 C 1.1372(4) 0.4674(4) 0.7667(3) 0.0189(7) Uani 1 1 d .
H21A H 1.2097 0.4463 0.7463 0.023 Uiso 1 1 calc R
H21B H 1.1263 0.5266 0.7295 0.023 Uiso 1 1 calc R
C22 C 1.2725(4) 0.6628(4) 0.9602(3) 0.0174(7) Uani 1 1 d .
H22A H 1.2555 0.7223 0.9263 0.021 Uiso 1 1 calc R
H22B H 1.3469 0.6482 0.9375 0.021 Uiso 1 1 calc R
C23 C 1.3025(3) 0.7307(4) 1.1043(3) 0.0173(7) Uani 1 1 d .
H23A H 1.3127 0.6686 1.1379 0.021 Uiso 1 1 calc R
H23B H 1.3837 0.8133 1.1436 0.021 Uiso 1 1 calc R
C24 C 1.2255(4) 0.8346(4) 1.2732(4) 0.0194(7) Uani 1 1 d .
H24A H 1.1669 0.8795 1.2910 0.023 Uiso 1 1 calc R
H24B H 1.3139 0.9063 1.3129 0.023 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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Hg Hg -2.3894 9.2266 '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
C1 Hg1 C14 175.96(15) . .
C2 Hg2 C7 174.60(14) . .
C8 Hg3 C13 174.54(14) . .
H1W O1W H2W 101(6) . .
C20 O1 C19 114.1(3) . .
C22 O2 C21 111.4(3) . .
C24 O3 C23 112.4(3) . .
C6 C1 C2 118.1(3) . .
C6 C1 Hg1 120.2(3) . .
C2 C1 Hg1 121.6(3) . .
C3 C2 C1 118.3(3) . .
C3 C2 Hg2 120.4(3) . .
C1 C2 Hg2 121.3(2) . .
F3 C3 C4 117.7(3) . .
F3 C3 C2 120.1(3) . .
C4 C3 C2 122.3(3) . .
F4 C4 C5 119.3(3) . .
F4 C4 C3 120.6(3) . .
C5 C4 C3 120.1(3) . .
F5 C5 C4 120.2(3) . .
F5 C5 C6 121.2(4) . .
C4 C5 C6 118.5(3) . .
F6 C6 C5 117.3(3) . .
F6 C6 C1 119.9(3) . .
C5 C6 C1 122.7(3) . .
C12 C7 C8 118.2(3) . .
C12 C7 Hg2 119.1(3) . .
C8 C7 Hg2 122.7(2) . .
C9 C8 C7 118.5(3) . .
C9 C8 Hg3 120.5(3) . .
C7 C8 Hg3 120.9(3) . .
F9 C9 C8 120.0(3) . .
F9 C9 C10 117.5(3) . .
C8 C9 C10 122.5(3) . .
F10 C10 C11 119.5(3) . .
F10 C10 C9 121.2(3) . .
C11 C10 C9 119.3(3) . .
F11 C11 C10 120.1(3) . .
F11 C11 C12 121.1(3) . .
C10 C11 C12 118.8(3) . .
F12 C12 C7 120.0(3) . .
F12 C12 C11 117.3(3) . .
C7 C12 C11 122.7(3) . .
C18 C13 C14 118.5(3) . .
C18 C13 Hg3 119.1(3) . .
C14 C13 Hg3 122.3(2) . .
C15 C14 C13 118.0(3) . .
C15 C14 Hg1 120.1(3) . .
C13 C14 Hg1 121.9(2) . .
F15 C15 C14 120.1(3) . .
F15 C15 C16 117.4(3) . .
C14 C15 C16 122.5(3) . .
F16 C16 C17 120.3(3) . .
F16 C16 C15 120.5(4) . .
C17 C16 C15 119.2(3) . .
F17 C17 C16 119.7(3) . .
F17 C17 C18 121.0(4) . .
C16 C17 C18 119.2(3) . .
F18 C18 C17 117.0(3) . .
F18 C18 C13 120.5(3) . .
C17 C18 C13 122.5(4) . .
O1 C19 C24 113.6(3) . 2_767
O1 C19 H19A 108.8 . .
C24 C19 H19A 108.8 2_767 .
O1 C19 H19B 108.8 . .
C24 C19 H19B 108.8 2_767 .
H19A C19 H19B 107.7 . .
O1 C20 C21 108.7(3) . .
O1 C20 H20A 109.9 . .
C21 C20 H20A 109.9 . .
O1 C20 H20B 109.9 . .
C21 C20 H20B 109.9 . .
H20A C20 H20B 108.3 . .
O2 C21 C20 109.8(3) . .
O2 C21 H21A 109.7 . .
C20 C21 H21A 109.7 . .
O2 C21 H21B 109.7 . .
C20 C21 H21B 109.7 . .
H21A C21 H21B 108.2 . .
O2 C22 C23 110.6(3) . .
O2 C22 H22A 109.5 . .
C23 C22 H22A 109.5 . .
O2 C22 H22B 109.5 . .
C23 C22 H22B 109.5 . .
H22A C22 H22B 108.1 . .
O3 C23 C22 109.5(3) . .
O3 C23 H23A 109.8 . .
C22 C23 H23A 109.8 . .
O3 C23 H23B 109.8 . .
C22 C23 H23B 109.8 . .
H23A C23 H23B 108.2 . .
O3 C24 C19 114.0(3) . 2_767
O3 C24 H24A 108.7 . .
C19 C24 H24A 108.7 2_767 .
O3 C24 H24B 108.7 . .
C19 C24 H24B 108.7 2_767 .
H24A C24 H24B 107.6 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Hg1 C1 2.065(4) .
Hg1 C14 2.072(3) .
Hg2 C2 2.074(4) .
Hg2 C7 2.077(4) .
Hg3 C8 2.067(3) .
Hg3 C13 2.069(4) .
F3 C3 1.356(4) .
F4 C4 1.352(4) .
F5 C5 1.340(4) .
F6 C6 1.350(4) .
F9 C9 1.354(4) .
F10 C10 1.345(4) .
F11 C11 1.339(4) .
F12 C12 1.353(4) .
F15 C15 1.353(4) .
F16 C16 1.350(4) .
F17 C17 1.344(4) .
F18 C18 1.356(4) .
O1W H1W 0.77(7) .
O1W H2W 0.82(7) .
O1 C20 1.425(5) .
O1 C19 1.432(4) .
O2 C22 1.425(4) .
O2 C21 1.427(4) .
O3 C24 1.423(4) .
O3 C23 1.430(5) .
C1 C6 1.393(5) .
C1 C2 1.422(5) .
C2 C3 1.390(5) .
C3 C4 1.382(5) .
C4 C5 1.379(6) .
C5 C6 1.391(5) .
C7 C12 1.382(5) .
C7 C8 1.415(5) .
C8 C9 1.376(5) .
C9 C10 1.389(5) .
C10 C11 1.379(5) .
C11 C12 1.385(6) .
C13 C18 1.383(5) .
C13 C14 1.420(5) .
C14 C15 1.374(5) .
C15 C16 1.390(5) .
C16 C17 1.374(6) .
C17 C18 1.374(5) .
C19 C24 1.521(5) 2_767
C19 H19A 0.9900 .
C19 H19B 0.9900 .
C20 C21 1.501(5) .
C20 H20A 0.9900 .
C20 H20B 0.9900 .
C21 H21A 0.9900 .
C21 H21B 0.9900 .
C22 C23 1.504(5) .
C22 H22A 0.9900 .
C22 H22B 0.9900 .
C23 H23A 0.9900 .
C23 H23B 0.9900 .
C24 C19 1.521(5) 2_767
C24 H24A 0.9900 .
C24 H24B 0.9900 .
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_4
C6 C1 C2 C3 0.6(5) .
Hg1 C1 C2 C3 175.9(3) .
C6 C1 C2 Hg2 -177.4(3) .
Hg1 C1 C2 Hg2 -2.2(4) .
C1 C2 C3 F3 -179.4(3) .
Hg2 C2 C3 F3 -1.4(5) .
C1 C2 C3 C4 0.4(5) .
Hg2 C2 C3 C4 178.5(3) .
F3 C3 C4 F4 -0.1(5) .
C2 C3 C4 F4 -179.9(3) .
F3 C3 C4 C5 178.2(3) .
C2 C3 C4 C5 -1.6(6) .
F4 C4 C5 F5 1.3(6) .
C3 C4 C5 F5 -177.1(3) .
F4 C4 C5 C6 -180.0(3) .
C3 C4 C5 C6 1.7(6) .
F5 C5 C6 F6 -1.0(5) .
C4 C5 C6 F6 -179.7(3) .
F5 C5 C6 C1 178.1(3) .
C4 C5 C6 C1 -0.6(6) .
C2 C1 C6 F6 178.5(3) .
Hg1 C1 C6 F6 3.2(5) .
C2 C1 C6 C5 -0.5(6) .
Hg1 C1 C6 C5 -175.8(3) .
C12 C7 C8 C9 0.6(5) .
Hg2 C7 C8 C9 -178.4(3) .
C12 C7 C8 Hg3 -176.5(3) .
Hg2 C7 C8 Hg3 4.5(4) .
C7 C8 C9 F9 -178.8(3) .
Hg3 C8 C9 F9 -1.6(5) .
C7 C8 C9 C10 1.2(6) .
Hg3 C8 C9 C10 178.4(3) .
F9 C9 C10 F10 0.7(5) .
C8 C9 C10 F10 -179.3(3) .
F9 C9 C10 C11 178.3(3) .
C8 C9 C10 C11 -1.6(6) .
F10 C10 C11 F11 -0.8(5) .
C9 C10 C11 F11 -178.5(3) .
F10 C10 C11 C12 177.8(3) .
C9 C10 C11 C12 0.1(6) .
C8 C7 C12 F12 178.3(3) .
Hg2 C7 C12 F12 -2.7(5) .
C8 C7 C12 C11 -2.2(5) .
Hg2 C7 C12 C11 176.9(3) .
F11 C11 C12 F12 0.0(5) .
C10 C11 C12 F12 -178.6(3) .
F11 C11 C12 C7 -179.6(3) .
C10 C11 C12 C7 1.8(6) .
C18 C13 C14 C15 -0.9(5) .
Hg3 C13 C14 C15 175.6(3) .
C18 C13 C14 Hg1 -177.9(3) .
Hg3 C13 C14 Hg1 -1.4(4) .
C13 C14 C15 F15 -176.8(3) .
Hg1 C14 C15 F15 0.3(5) .
C13 C14 C15 C16 3.0(6) .
Hg1 C14 C15 C16 -179.9(3) .
F15 C15 C16 F16 -0.6(5) .
C14 C15 C16 F16 179.6(3) .
F15 C15 C16 C17 177.0(3) .
C14 C15 C16 C17 -2.8(6) .
F16 C16 C17 F17 -0.2(6) .
C15 C16 C17 F17 -177.8(3) .
F16 C16 C17 C18 178.1(3) .
C15 C16 C17 C18 0.5(6) .
F17 C17 C18 F18 1.2(5) .
C16 C17 C18 F18 -177.1(3) .
F17 C17 C18 C13 179.8(3) .
C16 C17 C18 C13 1.5(6) .
C14 C13 C18 F18 177.2(3) .
Hg3 C13 C18 F18 0.6(5) .
C14 C13 C18 C17 -1.3(6) .
Hg3 C13 C18 C17 -177.9(3) .
C20 O1 C19 C24 64.8(4) 2_767
C19 O1 C20 C21 176.8(3) .
C22 O2 C21 C20 -176.5(3) .
O1 C20 C21 O2 68.5(4) .
C21 O2 C22 C23 -177.4(3) .
C24 O3 C23 C22 -178.2(3) .
O2 C22 C23 O3 -65.9(4) .
C23 O3 C24 C19 -74.7(4) 2_767
