#------------------------------------------------------------------------------
#$Date: 2016-03-21 02:58:29 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178414 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/35/4023541.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_4023541
loop_
_publ_author_name
'Kohei Ogawa'
'Shinya Minegishi'
'Koichi Komatsu'
'Toshikazu Kitagawa'
_publ_contact_author_address
;
    Department of Chemistry for Materials, Graduate School of Engineering, 
    Mie University, Tsu, Mie 514-8507, Japan. 
;
_publ_contact_author_email       ' kitagawa@chem.mie-u.ac.jp'
_publ_contact_author_fax         ' +81-59-231-9416 '
_publ_contact_author_name        ' Toshikazu Kitagawa '
_publ_contact_author_phone       ' +81-59-231-9416 '
_publ_section_title
;
 Generation and Reaction of a Phenyl-Substituted Cyclopentadienyl
 Cation Annelated with Two Homoadamantene Frameworks
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5248
_journal_page_last               5254
_journal_paper_doi               10.1021/jo800340g
_journal_volume                  73
_journal_year                    2008
_chemical_formula_moiety         'C29 H33, F6 Sb'
_chemical_formula_sum            'C29 H33 F6 Sb'
_chemical_formula_weight         617.30
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_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                 100.848(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.0120(13)
_cell_length_b                   21.486(3)
_cell_length_c                   11.6831(16)
_cell_measurement_temperature    100(2)
_cell_volume                     2468.3(6)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_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      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'CCD area detector'
_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  0.0423
_diffrn_reflns_av_sigmaI/netI    0.0549
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            12263
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.01
_exptl_absorpt_coefficient_mu    1.180
_exptl_absorpt_correction_T_max  0.8911
_exptl_absorpt_correction_T_min  0.8911
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            'reddish orange'
_exptl_crystal_density_diffrn    1.661
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1248
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         1.335
_refine_diff_density_min         -0.810
_refine_diff_density_rms         0.100
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     325
_refine_ls_number_reflns         4333
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0558
_refine_ls_R_factor_gt           0.0378
_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)+(0.0300P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0726
_refine_ls_wR_factor_ref         0.0759
_reflns_number_gt                3396
_reflns_number_total             4333
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo800340g-File004.cif
_cod_data_source_block           8+B(C6F5)4-
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4023541
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
Sb1 Sb 0.23104(3) 0.166805(13) 0.01040(2) 0.02097(10) Uani 1 1 d . . .
F1 F 0.3931(2) 0.20940(11) 0.0047(2) 0.0365(6) Uani 1 1 d . . .
F5 F 0.1400(2) 0.21435(11) -0.1149(2) 0.0387(7) Uani 1 1 d . . .
F3 F 0.1865(3) 0.22514(11) 0.1145(2) 0.0453(7) Uani 1 1 d . . .
F4 F 0.0712(2) 0.12260(12) 0.0161(2) 0.0364(6) Uani 1 1 d . . .
F2 F 0.3227(2) 0.11894(11) 0.1345(2) 0.0381(7) Uani 1 1 d . . .
F6 F 0.2729(3) 0.10760(11) -0.0946(2) 0.0420(7) Uani 1 1 d . . .
C17 C 1.0016(4) 0.09155(18) 0.2825(3) 0.0236(9) Uani 1 1 d . . .
H17A H 1.0594 0.1051 0.2271 0.028 Uiso 1 1 calc R . .
H17B H 1.0549 0.0623 0.3387 0.028 Uiso 1 1 calc R . .
C8 C 0.7558(3) 0.15805(17) -0.0466(3) 0.0159(8) Uani 1 1 d . . .
C10 C 0.7925(4) 0.10522(17) 0.1322(3) 0.0176(9) Uani 1 1 d . . .
C16 C 0.8753(4) 0.05880(18) 0.2164(3) 0.0214(9) Uani 1 1 d . . .
H16 H 0.9035 0.0232 0.1711 0.026 Uiso 1 1 calc R . .
C12 C 0.6705(4) 0.14030(19) 0.1724(4) 0.0245(10) Uani 1 1 d . . .
H12 H 0.5899 0.1483 0.1092 0.029 Uiso 1 1 calc R . .
C7 C 0.7797(4) 0.20361(18) 0.0410(3) 0.0168(9) Uani 1 1 d . . .
C11 C 0.8023(4) 0.17328(17) 0.1566(3) 0.0183(9) Uani 1 1 d . . .
C29 C 0.5821(4) 0.03721(18) -0.1190(3) 0.0213(9) Uani 1 1 d . . .
H29A H 0.5567 -0.0068 -0.1358 0.026 Uiso 1 1 calc R . .
H29B H 0.5240 0.0535 -0.0661 0.026 Uiso 1 1 calc R . .
C5 C 0.8363(4) 0.36545(19) -0.0590(3) 0.0212(9) Uani 1 1 d . . .
H5 H 0.8751 0.3859 -0.1170 0.025 Uiso 1 1 calc R . .
C25 C 0.7936(4) 0.06639(19) -0.2566(3) 0.0254(10) Uani 1 1 d . . .
H25 H 0.8535 0.0514 -0.3103 0.030 Uiso 1 1 calc R . .
C3 C 0.7235(4) 0.37065(18) 0.1046(3) 0.0200(9) Uani 1 1 d . . .
H3 H 0.6848 0.3946 0.1585 0.024 Uiso 1 1 calc R . .
C27 C 0.7327(4) 0.03992(17) -0.0556(3) 0.0199(9) Uani 1 1 d . . .
H27 H 0.7478 0.0057 0.0035 0.024 Uiso 1 1 calc R . .
C20 C 0.9011(4) 0.19838(18) 0.2609(3) 0.0217(9) Uani 1 1 d . . .
H20A H 0.8535 0.2294 0.3014 0.026 Uiso 1 1 calc R . .
H20B H 0.9762 0.2200 0.2330 0.026 Uiso 1 1 calc R . .
C18 C 0.9610(4) 0.14807(17) 0.3476(3) 0.0210(9) Uani 1 1 d . . .
H18 H 1.0456 0.1653 0.3966 0.025 Uiso 1 1 calc R . .
C13 C 0.6376(4) 0.1259(2) 0.2901(4) 0.0277(10) Uani 1 1 d . . .
H13A H 0.5510 0.1025 0.2786 0.033 Uiso 1 1 calc R . .
H13B H 0.6230 0.1657 0.3288 0.033 Uiso 1 1 calc R . .
C15 C 0.7927(4) 0.03414(19) 0.3036(4) 0.0264(10) Uani 1 1 d . . .
H15A H 0.8493 0.0054 0.3588 0.032 Uiso 1 1 calc R . .
H15B H 0.7130 0.0107 0.2620 0.032 Uiso 1 1 calc R . .
C21 C 0.7115(4) 0.16809(18) -0.1767(3) 0.0187(8) Uani 1 1 d . . .
H21 H 0.7130 0.2138 -0.1923 0.022 Uiso 1 1 calc R . .
C26 C 0.8307(4) 0.02921(19) -0.1424(4) 0.0249(10) Uani 1 1 d . . .
H26A H 0.9240 0.0407 -0.1035 0.030 Uiso 1 1 calc R . .
H26B H 0.8311 -0.0157 -0.1615 0.030 Uiso 1 1 calc R . .
C9 C 0.7616(3) 0.09952(17) 0.0063(3) 0.0162(8) Uani 1 1 d . . .
C23 C 0.5529(4) 0.07388(18) -0.2326(3) 0.0231(10) Uani 1 1 d . . .
H23 H 0.4573 0.0644 -0.2715 0.028 Uiso 1 1 calc R . .
C6 C 0.8350(4) 0.30141(19) -0.0544(3) 0.0205(9) Uani 1 1 d . . .
H6 H 0.8737 0.2779 -0.1089 0.025 Uiso 1 1 calc R . .
C1 C 0.7771(4) 0.27068(18) 0.0300(3) 0.0172(9) Uani 1 1 d . . .
C24 C 0.6463(4) 0.0514(2) -0.3133(4) 0.0294(10) Uani 1 1 d . . .
H24A H 0.6227 0.0725 -0.3898 0.035 Uiso 1 1 calc R . .
H24B H 0.6355 0.0060 -0.3261 0.035 Uiso 1 1 calc R . .
C14 C 0.7443(4) 0.08894(19) 0.3711(4) 0.0265(10) Uani 1 1 d . . .
H14 H 0.7002 0.0710 0.4337 0.032 Uiso 1 1 calc R . .
C19 C 0.8666(4) 0.1272(2) 0.4304(3) 0.0265(10) Uani 1 1 d . . .
H19A H 0.9201 0.1021 0.4941 0.032 Uiso 1 1 calc R . .
H19B H 0.8333 0.1645 0.4660 0.032 Uiso 1 1 calc R . .
C2 C 0.7223(4) 0.30669(19) 0.1102(3) 0.0200(9) Uani 1 1 d . . .
H2 H 0.6838 0.2867 0.1689 0.024 Uiso 1 1 calc R . .
C28 C 0.8120(4) 0.13595(18) -0.2445(3) 0.0230(9) Uani 1 1 d . . .
H28A H 0.8004 0.1545 -0.3233 0.028 Uiso 1 1 calc R . .
H28B H 0.9061 0.1447 -0.2039 0.028 Uiso 1 1 calc R . .
C22 C 0.5654(4) 0.14447(18) -0.2197(3) 0.0210(9) Uani 1 1 d . . .
H22A H 0.5080 0.1585 -0.1643 0.025 Uiso 1 1 calc R . .
H22B H 0.5292 0.1639 -0.2961 0.025 Uiso 1 1 calc R . .
C4 C 0.7813(4) 0.40001(19) 0.0204(3) 0.0204(9) Uani 1 1 d . . .
H4 H 0.7832 0.4442 0.0172 0.024 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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Sb Sb -0.5866 1.5461 '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
F3 Sb1 F6 179.05(12) . . ?
F3 Sb1 F2 90.36(12) . . ?
F6 Sb1 F2 89.81(12) . . ?
F3 Sb1 F4 90.41(11) . . ?
F6 Sb1 F4 88.65(11) . . ?
F2 Sb1 F4 89.51(10) . . ?
F3 Sb1 F5 90.13(12) . . ?
F6 Sb1 F5 89.69(11) . . ?
F2 Sb1 F5 179.48(12) . . ?
F4 Sb1 F5 90.62(11) . . ?
F3 Sb1 F1 90.57(11) . . ?
F6 Sb1 F1 90.37(11) . . ?
F2 Sb1 F1 89.69(10) . . ?
F4 Sb1 F1 178.74(11) . . ?
F5 Sb1 F1 90.17(10) . . ?
C16 C17 C18 110.3(3) . . ?
C9 C8 C7 108.5(3) . . ?
C9 C8 C21 123.4(3) . . ?
C7 C8 C21 127.5(3) . . ?
C9 C10 C11 105.7(3) . . ?
C9 C10 C16 125.7(3) . . ?
C11 C10 C16 120.6(3) . . ?
C9 C10 C12 108.2(3) . . ?
C11 C10 C12 60.1(2) . . ?
C16 C10 C12 118.4(3) . . ?
C15 C16 C17 108.9(3) . . ?
C15 C16 C10 111.1(3) . . ?
C17 C16 C10 108.8(3) . . ?
C13 C12 C11 122.9(4) . . ?
C13 C12 C10 119.2(3) . . ?
C11 C12 C10 57.0(2) . . ?
C8 C7 C1 129.2(4) . . ?
C8 C7 C11 109.6(3) . . ?
C1 C7 C11 121.2(3) . . ?
C7 C11 C10 105.3(3) . . ?
C7 C11 C20 122.8(3) . . ?
C10 C11 C20 120.8(3) . . ?
C7 C11 C12 108.9(3) . . ?
C10 C11 C12 62.9(2) . . ?
C20 C11 C12 120.8(3) . . ?
C23 C29 C27 114.0(3) . . ?
C6 C5 C4 120.2(4) . . ?
C28 C25 C24 109.8(3) . . ?
C28 C25 C26 115.3(3) . . ?
C24 C25 C26 108.8(3) . . ?
C2 C3 C4 119.8(4) . . ?
C9 C27 C29 110.5(3) . . ?
C9 C27 C26 111.0(3) . . ?
C29 C27 C26 111.0(3) . . ?
C11 C20 C18 113.4(3) . . ?
C20 C18 C17 109.9(3) . . ?
C20 C18 C19 114.4(3) . . ?
C17 C18 C19 109.4(3) . . ?
C12 C13 C14 115.4(3) . . ?
C16 C15 C14 109.8(3) . . ?
C8 C21 C22 111.2(3) . . ?
C8 C21 C28 110.6(3) . . ?
C22 C21 C28 110.7(3) . . ?
C25 C26 C27 114.1(3) . . ?
C8 C9 C10 110.8(3) . . ?
C8 C9 C27 125.3(3) . . ?
C10 C9 C27 123.8(3) . . ?
C29 C23 C22 115.4(3) . . ?
C29 C23 C24 109.6(3) . . ?
C22 C23 C24 109.1(3) . . ?
C5 C6 C1 120.4(4) . . ?
C6 C1 C2 118.4(4) . . ?
C6 C1 C7 122.0(3) . . ?
C2 C1 C7 119.5(3) . . ?
C23 C24 C25 108.5(3) . . ?
C13 C14 C19 114.4(3) . . ?
C13 C14 C15 109.5(3) . . ?
C19 C14 C15 109.9(3) . . ?
C14 C19 C18 113.9(3) . . ?
C3 C2 C1 120.7(4) . . ?
C25 C28 C21 114.1(3) . . ?
C23 C22 C21 114.5(3) . . ?
C5 C4 C3 120.4(4) . . ?
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
Sb1 F3 1.858(2) . ?
Sb1 F6 1.868(2) . ?
Sb1 F2 1.871(2) . ?
Sb1 F4 1.873(2) . ?
Sb1 F5 1.874(2) . ?
Sb1 F1 1.875(2) . ?
C17 C16 1.524(5) . ?
C17 C18 1.528(5) . ?
C8 C9 1.398(5) . ?
C8 C7 1.404(5) . ?
C8 C21 1.517(5) . ?
C10 C9 1.450(5) . ?
C10 C11 1.490(5) . ?
C10 C16 1.530(5) . ?
C10 C12 1.580(5) . ?
C16 C15 1.523(5) . ?
C12 C13 1.506(5) . ?
C12 C11 1.539(5) . ?
C7 C1 1.447(5) . ?
C7 C11 1.478(5) . ?
C11 C20 1.516(5) . ?
C29 C23 1.524(5) . ?
C29 C27 1.551(5) . ?
C5 C6 1.377(5) . ?
C5 C4 1.381(5) . ?
C25 C28 1.509(5) . ?
C25 C24 1.533(6) . ?
C25 C26 1.539(5) . ?
C3 C2 1.376(5) . ?
C3 C4 1.384(5) . ?
C27 C9 1.472(5) . ?
C27 C26 1.555(5) . ?
C20 C18 1.525(5) . ?
C18 C19 1.541(5) . ?
C13 C14 1.513(6) . ?
C15 C14 1.545(5) . ?
C21 C22 1.540(5) . ?
C21 C28 1.554(5) . ?
C23 C22 1.527(5) . ?
C23 C24 1.527(5) . ?
C6 C1 1.400(5) . ?
C1 C2 1.404(5) . ?
C14 C19 1.528(6) . ?
