#------------------------------------------------------------------------------
#$Date: 2017-03-04 03:49:53 +0200 (Sat, 04 Mar 2017) $
#$Revision: 192938 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/34/53/4345371.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_4345371
loop_
_publ_author_name
'Bhowmik, Susovan'
'Kosa, Monica'
'Mizrahi, Amir'
'Fridman, Natalia'
'Saphier, Magal'
'Stanger, Amnon'
'Gross, Zeev'
_publ_section_title
;
 The Planar Cyclooctatetraene Bridge in Bis-Metallic Macrocycles:
 Isolating or Conjugating?
;
_journal_issue                   4
_journal_name_full               'Inorganic chemistry'
_journal_page_first              2287
_journal_page_last               2296
_journal_paper_doi               10.1021/acs.inorgchem.6b02944
_journal_volume                  56
_journal_year                    2017
_chemical_formula_moiety         'C74 H18 F30 N8'
_chemical_formula_sum            'C74 H18 F30 N8'
_chemical_formula_weight         1588.96
_chemical_name_common            'Gross71 (Susovan)'
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                113.361(6)
_cell_angle_beta                 94.325(4)
_cell_angle_gamma                97.777(10)
_cell_formula_units_Z            1
_cell_length_a                   6.331(6)
_cell_length_b                   15.802(6)
_cell_length_c                   15.896(9)
_cell_measurement_reflns_used    4156
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      24.14
_cell_measurement_theta_min      1.41
_cell_volume                     1431.8(17)
_computing_cell_refinement       'DENZO HKL2000 (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius, 2006)'
_computing_data_reduction        'DENZO HKL2000 (Otwinowski & Minor 1997)'
_computing_molecular_graphics    'Mercury 3.5'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      200(2)
_diffrn_detector_area_resol_mean 95
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'phi- and 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  0.0830
_diffrn_reflns_av_sigmaI/netI    0.0566
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       0
_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            4311
_diffrn_reflns_theta_full        24.14
_diffrn_reflns_theta_max         24.14
_diffrn_reflns_theta_min         1.41
_diffrn_standards_decay_%        none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_number         none
_exptl_absorpt_coefficient_mu    0.179
_exptl_absorpt_correction_T_max  0.9741
_exptl_absorpt_correction_T_min  0.9238
_exptl_absorpt_process_details
; 
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'  
;
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.843
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             788
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.365
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     517
_refine_ls_number_reflns         4311
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.1011
_refine_ls_R_factor_gt           0.0673
_refine_ls_shift/su_max          0.020
_refine_ls_shift/su_mean         0.004
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1115P)²+1.0115P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1750
_refine_ls_wR_factor_ref         0.1955
_reflns_number_gt                2978
_reflns_number_total             4311
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic6b02944_si_004.cif
_cod_data_source_block           Gross71
_cod_original_cell_volume        1431.8(16)
_cod_database_code               4345371
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
F1 F 0.5712(5) 0.1690(2) 0.5603(2) 0.0852(10) Uani 1 1 d .
F2 F 0.5055(6) 0.0944(3) 0.6820(3) 0.1006(12) Uani 1 1 d .
F3 F 0.8290(6) 0.1112(3) 0.8092(3) 0.0945(12) Uani 1 1 d .
F4 F 1.2238(6) 0.1972(2) 0.8097(2) 0.0816(10) Uani 1 1 d .
F5 F 1.2940(5) 0.2769(2) 0.6917(2) 0.0665(8) Uani 1 1 d .
F6 F 1.6974(4) 0.16474(19) 0.32963(19) 0.0633(8) Uani 1 1 d .
F7 F 1.8705(4) 0.0176(2) 0.2317(2) 0.0660(8) Uani 1 1 d .
F8 F 1.6718(5) -0.10622(19) 0.06286(19) 0.0668(8) Uani 1 1 d .
F9 F 1.2846(5) -0.08710(18) -0.00325(18) 0.0635(8) Uani 1 1 d .
F10 F 1.1016(4) 0.05468(19) 0.09650(17) 0.0578(7) Uani 1 1 d .
F11 F 0.6963(5) 0.26414(19) 0.0232(2) 0.0727(9) Uani 1 1 d .
F12 F 0.6096(6) 0.3041(3) -0.1226(2) 0.0900(11) Uani 1 1 d .
F13 F 0.6694(5) 0.4833(3) -0.1036(2) 0.0842(10) Uani 1 1 d .
F14 F 0.8276(5) 0.6231(2) 0.0632(2) 0.0779(9) Uani 1 1 d .
F15 F 0.9406(5) 0.58420(19) 0.2067(2) 0.0671(8) Uani 1 1 d .
N1 N 0.8353(7) 0.3666(3) 0.4852(3) 0.0564(11) Uani 1 1 d .
H1 H 0.882(8) 0.334(3) 0.429(4) 0.067(15) Uiso 1 1 d .
N2 N 1.1385(6) 0.2592(3) 0.4197(2) 0.0459(9) Uani 1 1 d .
H2 H 1.184(13) 0.328(6) 0.439(6) 0.15(3) Uiso 1 1 d .
N3 N 1.0793(6) 0.3104(3) 0.2601(3) 0.0480(10) Uani 1 1 d .
H3 H 1.017(11) 0.327(5) 0.309(5) 0.11(2) Uiso 1 1 d .
N4 N 0.1957(7) 0.5888(3) 0.6488(3) 0.0593(11) Uani 1 1 d .
C1 C 0.6936(8) 0.4260(3) 0.4919(3) 0.0497(12) Uani 1 1 d .
C2 C 0.6115(7) 0.4418(3) 0.5764(3) 0.0428(10) Uani 1 1 d .
C3 C 0.7083(7) 0.3893(3) 0.6151(3) 0.0432(10) Uani 1 1 d .
H3A H 0.6846 0.3869 0.6725 0.052 Uiso 1 1 calc R
C4 C 0.8455(7) 0.3409(3) 0.5567(3) 0.0458(11) Uani 1 1 d .
C5 C 0.9625(7) 0.2711(3) 0.5563(3) 0.0427(10) Uani 1 1 d .
C6 C 1.0861(7) 0.2292(3) 0.4881(3) 0.0436(10) Uani 1 1 d .
C7 C 1.1577(7) 0.1432(3) 0.4662(3) 0.0474(11) Uani 1 1 d .
H7 H 1.1440 0.1062 0.5008 0.057 Uiso 1 1 calc R
C8 C 1.2488(7) 0.1222(3) 0.3882(3) 0.0482(11) Uani 1 1 d .
H8 H 1.3115 0.0683 0.3594 0.058 Uiso 1 1 calc R
C9 C 1.2361(7) 0.1934(3) 0.3560(3) 0.0432(10) Uani 1 1 d .
C10 C 1.2876(7) 0.1947(3) 0.2735(3) 0.0445(11) Uani 1 1 d .
C11 C 1.2245(7) 0.2525(3) 0.2313(3) 0.0468(11) Uani 1 1 d .
C12 C 1.2798(7) 0.2561(3) 0.1486(3) 0.0468(11) Uani 1 1 d .
H12 H 1.3828 0.2245 0.1139 0.056 Uiso 1 1 calc R
C13 C 1.1637(8) 0.3115(3) 0.1262(3) 0.0499(12) Uani 1 1 d .
H13 H 1.1695 0.3251 0.0732 0.060 Uiso 1 1 calc R
C14 C 1.0302(8) 0.3461(3) 0.1966(3) 0.0478(11) Uani 1 1 d .
C15 C 0.8764(7) 0.4013(3) 0.2016(3) 0.0436(11) Uani 1 1 d .
C16 C 0.2376(8) 0.5659(3) 0.7219(3) 0.0499(12) Uani 1 1 d .
C17 C 0.3987(7) 0.5109(3) 0.7038(3) 0.0459(11) Uani 1 1 d .
H17 H 0.4582 0.4859 0.7437 0.055 Uiso 1 1 calc R
C18 C 0.4562(7) 0.4990(3) 0.6188(3) 0.0444(11) Uani 1 1 d .
C19 C 0.3282(8) 0.5505(3) 0.5856(3) 0.0535(12) Uani 1 1 d .
C20 C 0.9325(7) 0.2299(3) 0.6249(3) 0.0419(10) Uani 1 1 d .
C21 C 0.7357(8) 0.1807(3) 0.6242(4) 0.0569(13) Uani 1 1 d .
C22 C 0.7000(8) 0.1415(4) 0.6846(4) 0.0616(14) Uani 1 1 d .
C23 C 0.8610(10) 0.1490(4) 0.7477(4) 0.0649(15) Uani 1 1 d .
C24 C 1.0617(9) 0.1920(4) 0.7487(3) 0.0583(13) Uani 1 1 d .
C25 C 1.0944(7) 0.2322(3) 0.6875(3) 0.0496(11) Uani 1 1 d .
C26 C 1.3964(7) 0.1171(3) 0.2166(3) 0.0447(11) Uani 1 1 d .
C27 C 1.5908(7) 0.1039(3) 0.2473(3) 0.0448(11) Uani 1 1 d .
C28 C 1.6837(7) 0.0283(3) 0.1969(3) 0.0474(11) Uani 1 1 d .
C29 C 1.5824(8) -0.0341(3) 0.1128(3) 0.0475(11) Uani 1 1 d .
C30 C 1.3872(8) -0.0237(3) 0.0792(3) 0.0482(11) Uani 1 1 d .
C31 C 1.2952(7) 0.0499(3) 0.1308(3) 0.0448(11) Uani 1 1 d .
C32 C 0.8194(7) 0.4234(3) 0.1220(3) 0.0427(11) Uani 1 1 d .
C33 C 0.7329(8) 0.3539(3) 0.0359(3) 0.0499(11) Uani 1 1 d .
C34 C 0.6865(8) 0.3745(4) -0.0395(3) 0.0574(13) Uani 1 1 d .
C35 C 0.7152(8) 0.4634(4) -0.0295(4) 0.0601(14) Uani 1 1 d .
C36 C 0.7949(8) 0.5340(3) 0.0538(3) 0.0525(12) Uani 1 1 d .
C37 C 0.8483(7) 0.5128(3) 0.1270(3) 0.0502(12) Uani 1 1 d .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0033 0.0016 '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'
H H 0.0000 0.0000 '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
C4 N1 C1 112.5(4) . .
C4 N1 H1 123(3) . .
C1 N1 H1 121(3) . .
C9 N2 C6 109.3(3) . .
C9 N2 H2 122(5) . .
C6 N2 H2 118(5) . .
C11 N3 C14 110.4(4) . .
C11 N3 H3 131(5) . .
C14 N3 H3 118(5) . .
C19 N4 C16 108.2(4) . .
N1 C1 C2 105.8(4) . .
N1 C1 C19 113.2(4) . 2_666
C2 C1 C19 141.0(4) . 2_666
C3 C2 C1 106.7(3) . .
C3 C2 C18 123.4(4) . .
C1 C2 C18 129.9(4) . .
C2 C3 C4 109.3(4) . .
C2 C3 H3A 125.3 . .
C4 C3 H3A 125.3 . .
N1 C4 C3 105.7(4) . .
N1 C4 C5 120.8(4) . .
C3 C4 C5 133.3(4) . .
C6 C5 C4 123.7(4) . .
C6 C5 C20 116.6(4) . .
C4 C5 C20 119.2(4) . .
C5 C6 N2 125.2(4) . .
C5 C6 C7 127.7(4) . .
N2 C6 C7 106.5(4) . .
C8 C7 C6 108.9(4) . .
C8 C7 H7 125.6 . .
C6 C7 H7 125.6 . .
C7 C8 C9 109.1(4) . .
C7 C8 H8 125.4 . .
C9 C8 H8 125.4 . .
C10 C9 N2 125.2(4) . .
C10 C9 C8 128.3(4) . .
N2 C9 C8 106.2(4) . .
C9 C10 C11 127.5(4) . .
C9 C10 C26 115.7(4) . .
C11 C10 C26 116.2(4) . .
N3 C11 C12 106.5(4) . .
N3 C11 C10 125.1(4) . .
C12 C11 C10 128.1(4) . .
C13 C12 C11 109.3(4) . .
C13 C12 H12 125.3 . .
C11 C12 H12 125.3 . .
C12 C13 C14 107.6(4) . .
C12 C13 H13 126.2 . .
C14 C13 H13 126.2 . .
N3 C14 C15 124.9(4) . .
N3 C14 C13 105.9(4) . .
C15 C14 C13 129.1(4) . .
C14 C15 C16 123.0(4) . 2_666
C14 C15 C32 118.8(3) . .
C16 C15 C32 118.1(4) 2_666 .
N4 C16 C17 108.5(4) . .
N4 C16 C15 119.6(4) . 2_666
C17 C16 C15 131.9(4) . 2_666
C18 C17 C16 108.6(4) . .
C18 C17 H17 125.7 . .
C16 C17 H17 125.7 . .
C17 C18 C19 105.8(4) . .
C17 C18 C2 123.3(4) . .
C19 C18 C2 130.9(4) . .
N4 C19 C1 113.2(4) . 2_666
N4 C19 C18 108.8(4) . .
C1 C19 C18 138.0(4) 2_666 .
C21 C20 C25 115.4(4) . .
C21 C20 C5 120.6(4) . .
C25 C20 C5 124.0(4) . .
F1 C21 C22 117.7(5) . .
F1 C21 C20 119.4(4) . .
C22 C21 C20 122.9(5) . .
C23 C22 F2 119.0(5) . .
C23 C22 C21 119.8(5) . .
F2 C22 C21 121.2(5) . .
C22 C23 F3 120.9(5) . .
C22 C23 C24 120.2(5) . .
F3 C23 C24 118.9(5) . .
F4 C24 C23 120.4(5) . .
F4 C24 C25 120.4(5) . .
C23 C24 C25 119.1(5) . .
F5 C25 C24 117.9(4) . .
F5 C25 C20 119.6(4) . .
C24 C25 C20 122.4(5) . .
C27 C26 C31 116.0(4) . .
C27 C26 C10 122.9(4) . .
C31 C26 C10 121.0(4) . .
F6 C27 C26 119.7(4) . .
F6 C27 C28 117.7(4) . .
C26 C27 C28 122.6(4) . .
F7 C28 C29 120.7(4) . .
F7 C28 C27 119.8(4) . .
C29 C28 C27 119.5(4) . .
F8 C29 C28 120.1(4) . .
F8 C29 C30 119.9(4) . .
C28 C29 C30 120.0(4) . .
F9 C30 C31 120.4(4) . .
F9 C30 C29 119.8(4) . .
C31 C30 C29 119.8(4) . .
F10 C31 C30 117.3(4) . .
F10 C31 C26 120.6(4) . .
C30 C31 C26 122.1(4) . .
C37 C32 C33 115.1(4) . .
C37 C32 C15 123.2(4) . .
C33 C32 C15 121.7(4) . .
F11 C33 C32 120.3(4) . .
F11 C33 C34 118.2(4) . .
C32 C33 C34 121.5(4) . .
C35 C34 F12 120.5(5) . .
C35 C34 C33 120.3(5) . .
F12 C34 C33 119.3(5) . .
C34 C35 C36 120.3(5) . .
C34 C35 F13 120.0(5) . .
C36 C35 F13 119.6(5) . .
F14 C36 C35 120.2(4) . .
F14 C36 C37 120.7(5) . .
C35 C36 C37 119.0(5) . .
F15 C37 C36 117.1(4) . .
F15 C37 C32 119.2(4) . .
C36 C37 C32 123.7(5) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
F1 C21 1.337(6) .
F2 C22 1.340(6) .
F3 C23 1.345(5) .
F4 C24 1.329(6) .
F5 C25 1.344(5) .
F6 C27 1.337(5) .
F7 C28 1.327(5) .
F8 C29 1.332(5) .
F9 C30 1.341(5) .
F10 C31 1.327(5) .
F11 C33 1.335(5) .
F12 C34 1.345(6) .
F13 C35 1.354(6) .
F14 C36 1.341(6) .
F15 C37 1.340(5) .
N1 C4 1.351(6) .
N1 C1 1.364(5) .
N1 H1 0.93(5) .
N2 C9 1.387(5) .
N2 C6 1.392(5) .
N2 H2 0.99(8) .
N3 C11 1.361(5) .
N3 C14 1.375(6) .
N3 H3 0.86(7) .
N4 C19 1.364(6) .
N4 C16 1.366(6) .
C1 C2 1.418(6) .
C1 C19 1.423(6) 2_666
C2 C3 1.388(6) .
C2 C18 1.448(6) .
C3 C4 1.393(6) .
C3 H3A 0.9500 .
C4 C5 1.408(6) .
C5 C6 1.388(6) .
C5 C20 1.485(6) .
C6 C7 1.410(6) .
C7 C8 1.346(6) .
C7 H7 0.9500 .
C8 C9 1.416(6) .
C8 H8 0.9500 .
C9 C10 1.384(6) .
C10 C11 1.409(6) .
C10 C26 1.496(6) .
C11 C12 1.407(6) .
C12 C13 1.347(6) .
C12 H12 0.9500 .
C13 C14 1.431(6) .
C13 H13 0.9500 .
C14 C15 1.378(6) .
C15 C16 1.414(6) 2_666
C15 C32 1.472(6) .
C16 C17 1.402(6) .
C16 C15 1.414(6) 2_666
C17 C18 1.373(6) .
C17 H17 0.9500 .
C18 C19 1.432(6) .
C19 C1 1.423(6) 2_666
C20 C21 1.374(7) .
C20 C25 1.360(6) .
C21 C22 1.349(7) .
C22 C23 1.335(8) .
C23 C24 1.353(8) .
C24 C25 1.371(7) .
C26 C27 1.363(6) .
C26 C31 1.390(6) .
C27 C28 1.385(6) .
C28 C29 1.351(6) .
C29 C30 1.366(7) .
C30 C31 1.365(6) .
C32 C37 1.370(6) .
C32 C33 1.383(6) .
C33 C34 1.383(7) .
C34 C35 1.335(7) .
C35 C36 1.351(7) .
C36 C37 1.364(6) .
