#------------------------------------------------------------------------------
#$Date: 2016-03-21 08:01:09 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178590 $
#$URL: svn://www.crystallography.net/cod/cif/4/07/01/4070139.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_4070139
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         'C44 H20 F24 Hg6 O6'
_chemical_formula_sum            'C44 H20 F24 Hg6 O6'
_chemical_formula_weight         2304.14
_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   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                113.8890(10)
_cell_angle_beta                 104.5110(10)
_cell_angle_gamma                103.5090(10)
_cell_formula_units_Z            1
_cell_length_a                   10.8129(3)
_cell_length_b                   10.8204(3)
_cell_length_c                   12.4980(5)
_cell_measurement_reflns_used    8304
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      35.13
_cell_measurement_theta_min      2.24
_cell_volume                     1198.03(7)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_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, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART 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  0.0378
_diffrn_reflns_av_sigmaI/netI    0.0250
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            47818
_diffrn_reflns_theta_full        32.00
_diffrn_reflns_theta_max         32.00
_diffrn_reflns_theta_min         1.93
_exptl_absorpt_coefficient_mu    19.294
_exptl_absorpt_correction_T_max  0.391
_exptl_absorpt_correction_T_min  0.129
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'APEX II'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    3.194
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1028
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_refine_diff_density_max         1.756
_refine_diff_density_min         -1.323
_refine_diff_density_rms         0.170
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     369
_refine_ls_number_reflns         8311
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0253
_refine_ls_R_factor_gt           0.0204
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0195P)²+1.2725P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0433
_refine_ls_wR_factor_ref         0.0447
_reflns_number_gt                7454
_reflns_number_total             8311
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om900626j_si_001.cif
_cod_data_source_block           sr
_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_original_cell_volume        1198.02(7)
_cod_database_code               4070139
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 0.341103(12) 1.096204(13) 0.496842(11) 0.01677(3) Uani 1 1 d .
Hg2 Hg -0.020899(12) 0.871108(13) 0.321753(11) 0.01603(3) Uani 1 1 d .
Hg3 Hg 0.141623(12) 1.130230(13) 0.239000(11) 0.01607(3) Uani 1 1 d .
F3 F -0.0953(2) 0.6808(3) 0.4473(2) 0.0310(5) Uani 1 1 d .
F4 F 0.0558(2) 0.6472(2) 0.6339(2) 0.0279(5) Uani 1 1 d .
F5 F 0.3284(2) 0.8128(2) 0.76449(19) 0.0236(4) Uani 1 1 d .
F6 F 0.4515(2) 1.0150(2) 0.7100(2) 0.0248(4) Uani 1 1 d .
F9 F -0.0969(2) 1.1422(2) 0.0414(2) 0.0241(4) Uani 1 1 d .
F10 F -0.3716(2) 0.9947(2) -0.0711(2) 0.0265(4) Uani 1 1 d .
F11 F -0.4928(2) 0.7861(2) -0.0196(2) 0.0274(4) Uani 1 1 d .
F12 F -0.3392(2) 0.7318(2) 0.1489(2) 0.0246(4) Uani 1 1 d .
F15 F 0.6428(2) 1.3201(2) 0.60674(19) 0.0244(4) Uani 1 1 d .
F16 F 0.7702(2) 1.5000(2) 0.5360(2) 0.0255(4) Uani 1 1 d .
F17 F 0.6247(2) 1.5151(2) 0.3313(2) 0.0259(4) Uani 1 1 d .
F18 F 0.3539(2) 1.3555(2) 0.20436(19) 0.0234(4) Uani 1 1 d .
C1 C 0.2428(3) 0.9498(3) 0.5435(3) 0.0163(5) Uani 1 1 d .
C2 C 0.1005(3) 0.8621(3) 0.4744(3) 0.0171(5) Uani 1 1 d .
C3 C 0.0410(3) 0.7641(4) 0.5085(3) 0.0190(6) Uani 1 1 d .
C4 C 0.1162(3) 0.7454(4) 0.6043(3) 0.0192(6) Uani 1 1 d .
C5 C 0.2549(3) 0.8302(4) 0.6711(3) 0.0187(6) Uani 1 1 d .
C6 C 0.3156(3) 0.9317(3) 0.6401(3) 0.0169(6) Uani 1 1 d .
C7 C -0.1318(3) 0.9057(3) 0.1822(3) 0.0169(5) Uani 1 1 d .
C8 C -0.0693(3) 1.0116(3) 0.1536(3) 0.0173(6) Uani 1 1 d .
C9 C -0.1532(3) 1.0380(3) 0.0690(3) 0.0177(6) Uani 1 1 d .
C10 C -0.2944(3) 0.9647(4) 0.0101(3) 0.0192(6) Uani 1 1 d .
C11 C -0.3560(3) 0.8597(4) 0.0371(3) 0.0201(6) Uani 1 1 d .
C12 C -0.2738(3) 0.8326(4) 0.1226(3) 0.0192(6) Uani 1 1 d .
C13 C 0.3532(3) 1.2472(3) 0.3356(3) 0.0174(6) Uani 1 1 d .
C14 C 0.4279(3) 1.2373(3) 0.4398(3) 0.0187(6) Uani 1 1 d .
C15 C 0.5672(3) 1.3238(3) 0.5048(3) 0.0179(6) Uani 1 1 d .
C16 C 0.6350(3) 1.4181(3) 0.4702(3) 0.0186(6) Uani 1 1 d .
C17 C 0.5618(3) 1.4260(3) 0.3675(3) 0.0191(6) Uani 1 1 d .
C18 C 0.4223(3) 1.3411(3) 0.3030(3) 0.0181(6) Uani 1 1 d .
O1 O 0.1835(2) 0.5839(3) 0.1164(2) 0.0214(5) Uani 1 1 d .
O2 O -0.0738(2) 0.5747(3) 0.1604(2) 0.0207(5) Uani 1 1 d .
C19 C 0.2638(4) 0.5429(4) 0.0430(3) 0.0251(7) Uani 1 1 d .
H19A H 0.2628 0.4472 0.0273 0.030 Uiso 1 1 calc R
H19B H 0.3586 0.6120 0.0905 0.030 Uiso 1 1 calc R
C20 C 0.0970(3) 0.4664(4) 0.1217(3) 0.0225(6) Uani 1 1 d .
H20A H 0.1518 0.4193 0.1523 0.027 Uiso 1 1 calc R
H20B H 0.0279 0.3943 0.0377 0.027 Uiso 1 1 calc R
C21 C 0.0282(4) 0.5274(4) 0.2104(3) 0.0225(6) Uani 1 1 d .
H21A H -0.0149 0.4532 0.2286 0.027 Uiso 1 1 calc R
H21B H 0.0981 0.6094 0.2898 0.027 Uiso 1 1 calc R
C22 C -0.2080(3) 0.4606(4) 0.0822(3) 0.0232(6) Uani 1 1 d .
H22A H -0.2703 0.4770 0.1257 0.028 Uiso 1 1 calc R
H22B H -0.2020 0.3673 0.0671 0.028 Uiso 1 1 calc R
O1W O 0.2272(3) 0.8802(3) 0.2335(2) 0.0230(5) Uani 1 1 d .
H1W H 0.281(6) 0.923(6) 0.211(5) 0.047(15) Uiso 1 1 d .
H2W H 0.210(7) 0.800(7) 0.198(6) 0.061(19) Uiso 1 1 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'
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 176.27(13) . .
C7 Hg2 C2 173.49(13) . .
C8 Hg3 C13 175.94(13) . .
C6 C1 C2 118.6(3) . .
C6 C1 Hg1 120.6(2) . .
C2 C1 Hg1 120.8(2) . .
C3 C2 C1 118.2(3) . .
C3 C2 Hg2 118.8(2) . .
C1 C2 Hg2 123.0(2) . .
F3 C3 C2 120.2(3) . .
F3 C3 C4 117.3(3) . .
C2 C3 C4 122.5(3) . .
F4 C4 C5 119.6(3) . .
F4 C4 C3 121.1(3) . .
C5 C4 C3 119.3(3) . .
F5 C5 C4 119.6(3) . .
F5 C5 C6 121.5(3) . .
C4 C5 C6 118.9(3) . .
F6 C6 C1 120.5(3) . .
F6 C6 C5 117.0(3) . .
C1 C6 C5 122.5(3) . .
C12 C7 C8 118.1(3) . .
C12 C7 Hg2 119.5(2) . .
C8 C7 Hg2 122.1(2) . .
C9 C8 C7 118.2(3) . .
C9 C8 Hg3 120.1(2) . .
C7 C8 Hg3 121.6(2) . .
F9 C9 C10 116.9(3) . .
F9 C9 C8 119.9(3) . .
C10 C9 C8 123.2(3) . .
F10 C10 C9 121.1(3) . .
F10 C10 C11 120.2(3) . .
C9 C10 C11 118.7(3) . .
F11 C11 C10 120.0(3) . .
F11 C11 C12 121.2(3) . .
C10 C11 C12 118.9(3) . .
F12 C12 C11 116.8(3) . .
F12 C12 C7 120.4(3) . .
C11 C12 C7 122.8(3) . .
C18 C13 C14 118.4(3) . .
C18 C13 Hg3 120.7(2) . .
C14 C13 Hg3 120.8(2) . .
C15 C14 C13 118.2(3) . .
C15 C14 Hg1 118.5(2) . .
C13 C14 Hg1 123.2(2) . .
F15 C15 C14 120.4(3) . .
F15 C15 C16 117.2(3) . .
C14 C15 C16 122.4(3) . .
F16 C16 C17 120.5(3) . .
F16 C16 C15 120.3(3) . .
C17 C16 C15 119.2(3) . .
F17 C17 C16 120.5(3) . .
F17 C17 C18 120.8(3) . .
C16 C17 C18 118.7(3) . .
F18 C18 C13 120.4(3) . .
F18 C18 C17 116.5(3) . .
C13 C18 C17 123.1(3) . .
C20 O1 C19 114.2(3) . .
C21 O2 C22 113.8(3) . .
O1 C19 C22 111.2(3) . 2_565
O1 C19 H19A 109.4 . .
C22 C19 H19A 109.4 2_565 .
O1 C19 H19B 109.4 . .
C22 C19 H19B 109.4 2_565 .
H19A C19 H19B 108.0 . .
O1 C20 C21 108.3(3) . .
O1 C20 H20A 110.0 . .
C21 C20 H20A 110.0 . .
O1 C20 H20B 110.0 . .
C21 C20 H20B 110.0 . .
H20A C20 H20B 108.4 . .
O2 C21 C20 113.3(3) . .
O2 C21 H21A 108.9 . .
C20 C21 H21A 108.9 . .
O2 C21 H21B 108.9 . .
C20 C21 H21B 108.9 . .
H21A C21 H21B 107.7 . .
O2 C22 C19 110.2(3) . 2_565
O2 C22 H22A 109.6 . .
C19 C22 H22A 109.6 2_565 .
O2 C22 H22B 109.6 . .
C19 C22 H22B 109.6 2_565 .
H22A C22 H22B 108.1 . .
H1W O1W H2W 110(6) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Hg1 C1 2.062(3) .
Hg1 C14 2.066(3) .
Hg2 C7 2.076(3) .
Hg2 C2 2.081(3) .
Hg3 C8 2.072(3) .
Hg3 C13 2.078(3) .
F3 C3 1.351(4) .
F4 C4 1.344(4) .
F5 C5 1.346(4) .
F6 C6 1.354(4) .
F9 C9 1.363(4) .
F10 C10 1.342(4) .
F11 C11 1.339(4) .
F12 C12 1.358(4) .
F15 C15 1.352(4) .
F16 C16 1.342(4) .
F17 C17 1.340(4) .
F18 C18 1.358(4) .
C1 C6 1.379(4) .
C1 C2 1.415(4) .
C2 C3 1.381(4) .
C3 C4 1.386(4) .
C4 C5 1.377(5) .
C5 C6 1.387(5) .
C7 C12 1.386(4) .
C7 C8 1.409(4) .
C8 C9 1.381(4) .
C9 C10 1.378(4) .
C10 C11 1.384(5) .
C11 C12 1.385(5) .
C13 C18 1.375(4) .
C13 C14 1.409(5) .
C14 C15 1.384(4) .
C15 C16 1.390(4) .
C16 C17 1.376(5) .
C17 C18 1.382(4) .
O1 C20 1.429(4) .
O1 C19 1.429(4) .
O2 C21 1.431(4) .
O2 C22 1.435(4) .
C19 C22 1.511(5) 2_565
C19 H19A 0.9700 .
C19 H19B 0.9700 .
C20 C21 1.505(5) .
C20 H20A 0.9700 .
C20 H20B 0.9700 .
C21 H21A 0.9700 .
C21 H21B 0.9700 .
C22 C19 1.511(5) 2_565
C22 H22A 0.9700 .
C22 H22B 0.9700 .
O1W H1W 0.84(6) .
O1W H2W 0.75(6) .
