#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:12:37 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178425 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/46/4024662.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_4024662
loop_
_publ_author_name
'Steven J. Robbins'
'Michelle E. Thibault'
'Jason D. Masuda'
'David R. Ward'
'René T. Boeré'
'Peter W. Dibble'
_publ_contact_author_address
; 
Department of Chemistry and Biochemistry
University of Lethbridge
Lethbridge, AB Canada
T1K 3M4
;
_publ_contact_author_email       dibble@uleth.ca
_publ_contact_author_fax         +1-403-329-2045
_publ_contact_author_name        'Dibble, Peter W.'
_publ_contact_author_phone       +1-403-329-2308
_publ_section_title
;
X-ray Structures of Cyclophanes Derived from Naphtho[1,2-c:5,6-c]difuran
and the Synthesis, Structure, and Reaction Kinetics of Its
1,3,6,8-Tetrasilylated Derivative
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5192
_journal_page_last               5198
_journal_paper_doi               10.1021/jo900582r
_journal_volume                  74
_journal_year                    2009
_chemical_formula_moiety         'C38 H64 O2 Si4'
_chemical_formula_sum            'C38 H64 O2 Si4'
_chemical_formula_weight         665.25
_chemical_melting_point          504.4
_chemical_name_common
;
1,3,6,8-tetrakis(tert-butyldimethylsilyl)
naphtho[1,2-c:5,6-c]difuran
;
_chemical_name_systematic
;
 1,3,6,8-tetrakis(tert-butyldimethylsilyl)
naphtho[1,2-c:5,6-c]difuran
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_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
_audit_update_record
;
2008-04-25 # Formatted by publCIF
;
_cell_angle_alpha                72.0720(10)
_cell_angle_beta                 88.2660(10)
_cell_angle_gamma                79.7590(10)
_cell_formula_units_Z            1
_cell_length_a                   6.8355(5)
_cell_length_b                   11.3386(8)
_cell_length_c                   14.1413(10)
_cell_measurement_reflns_used    4983
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.16
_cell_measurement_theta_min      2.79
_cell_volume                     1025.84(13)
_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      173(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type
;
Bruker ApexII 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  0.0300
_diffrn_reflns_av_sigmaI/netI    0.0378
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9931
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         1.92
_diffrn_source_type              'Bruker D8'
_exptl_absorpt_coefficient_mu    0.174
_exptl_absorpt_correction_T_max  0.9916
_exptl_absorpt_correction_T_min  0.9028
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
SADABS (Sheldrick, 2004)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.077
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.333
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3604
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0526
_refine_ls_R_factor_gt           0.0391
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0452P)²+0.3484P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0893
_refine_ls_wR_factor_ref         0.0960
_reflns_number_gt                2921
_reflns_number_total             3604
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo900582r_si_001.cif
_cod_data_source_block           3b
_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 2.4.1 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-1
_cod_database_code               4024662
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
_atom_site_disorder_assembly
_atom_site_disorder_group
Si1 Si 0.30918(8) 0.21778(5) 0.26482(4) 0.02136(15) Uani 1 1 d . . .
Si2 Si -0.04464(8) 0.67203(5) 0.29189(4) 0.02083(15) Uani 1 1 d . . .
C2 C 0.4236(3) 0.37143(17) 0.38898(13) 0.0195(4) Uani 1 1 d . . .
O1 O 0.15117(18) 0.44372(11) 0.29361(9) 0.0226(3) Uani 1 1 d . . .
C4 C 0.1594(3) 0.53192(17) 0.34229(13) 0.0208(4) Uani 1 1 d . . .
C3 C 0.3285(3) 0.48848(16) 0.40354(13) 0.0189(4) Uani 1 1 d . . .
C1 C 0.3105(3) 0.34656(17) 0.32165(14) 0.0213(4) Uani 1 1 d . . .
C7 C 0.3957(3) 0.69571(17) 0.55824(14) 0.0235(4) Uani 1 1 d . . .
H7 H 0.3302 0.7717 0.5687 0.028 Uiso 1 1 calc R . .
C6 C 0.3196(3) 0.64947(18) 0.49334(14) 0.0238(4) Uani 1 1 d . . .
H6 H 0.1992 0.6945 0.4583 0.029 Uiso 1 1 calc R . .
C5 C 0.4124(3) 0.53485(17) 0.47460(13) 0.0194(4) Uani 1 1 d . . .
C13 C 0.0650(3) 0.79563(18) 0.19346(14) 0.0255(4) Uani 1 1 d . . .
C14 C 0.2315(3) 0.8374(2) 0.23816(17) 0.0358(5) Uani 1 1 d . . .
H14A H 0.2926 0.8970 0.1853 0.043 Uiso 1 1 calc R . .
H14B H 0.3324 0.7637 0.2704 0.043 Uiso 1 1 calc R . .
H14C H 0.1764 0.8781 0.2874 0.043 Uiso 1 1 calc R . .
C11 C -0.1645(3) 0.7409(2) 0.38782(15) 0.0310(5) Uani 1 1 d . . .
H11A H -0.3061 0.7722 0.3706 0.037 Uiso 1 1 calc R . .
H11B H -0.1005 0.8107 0.3903 0.037 Uiso 1 1 calc R . .
H11C H -0.1500 0.6761 0.4529 0.037 Uiso 1 1 calc R . .
C15 C -0.0972(3) 0.91022(19) 0.14853(16) 0.0382(6) Uani 1 1 d . . .
H15A H -0.1524 0.9453 0.2009 0.046 Uiso 1 1 calc R . .
H15B H -0.2031 0.8846 0.1184 0.046 Uiso 1 1 calc R . .
H15C H -0.0399 0.9741 0.0975 0.046 Uiso 1 1 calc R . .
C12 C -0.2347(3) 0.6126(2) 0.23559(16) 0.0326(5) Uani 1 1 d . . .
H12A H -0.2929 0.5507 0.2879 0.039 Uiso 1 1 calc R . .
H12B H -0.1715 0.5728 0.1872 0.039 Uiso 1 1 calc R . .
H12C H -0.3394 0.6831 0.2020 0.039 Uiso 1 1 calc R . .
C16 C 0.1526(4) 0.7423(2) 0.11073(16) 0.0402(6) Uani 1 1 d . . .
H16A H 0.0473 0.7169 0.0799 0.048 Uiso 1 1 calc R . .
H16B H 0.2568 0.6690 0.1391 0.048 Uiso 1 1 calc R . .
H16C H 0.2096 0.8070 0.0604 0.048 Uiso 1 1 calc R . .
C21 C 0.5013(3) 0.08007(18) 0.32945(16) 0.0328(5) Uani 1 1 d . . .
H21A H 0.4806 0.0567 0.4013 0.039 Uiso 1 1 calc R . .
H21B H 0.6337 0.1021 0.3155 0.039 Uiso 1 1 calc R . .
H21C H 0.4906 0.0089 0.3056 0.039 Uiso 1 1 calc R . .
C23 C 0.3600(3) 0.27844(19) 0.12785(14) 0.0272(5) Uani 1 1 d . . .
C26 C 0.3728(4) 0.1729(2) 0.07999(16) 0.0385(6) Uani 1 1 d . . .
H26A H 0.3969 0.2061 0.0088 0.046 Uiso 1 1 calc R . .
H26B H 0.2474 0.1406 0.0890 0.046 Uiso 1 1 calc R . .
H26C H 0.4821 0.1046 0.1116 0.046 Uiso 1 1 calc R . .
C24 C 0.1924(4) 0.3854(2) 0.07541(16) 0.0418(6) Uani 1 1 d . . .
H24A H 0.1839 0.4542 0.1044 0.050 Uiso 1 1 calc R . .
H24B H 0.0661 0.3543 0.0837 0.050 Uiso 1 1 calc R . .
H24C H 0.2198 0.4163 0.0044 0.050 Uiso 1 1 calc R . .
C22 C 0.0576(3) 0.1748(2) 0.28487(18) 0.0379(5) Uani 1 1 d . . .
H22A H 0.0391 0.1215 0.2441 0.045 Uiso 1 1 calc R . .
H22B H -0.0435 0.2515 0.2659 0.045 Uiso 1 1 calc R . .
H22C H 0.0448 0.1288 0.3552 0.045 Uiso 1 1 calc R . .
C25 C 0.5565(4) 0.3273(2) 0.11383(18) 0.0452(6) Uani 1 1 d . . .
H25A H 0.5810 0.3601 0.0427 0.054 Uiso 1 1 calc R . .
H25B H 0.6650 0.2585 0.1457 0.054 Uiso 1 1 calc R . .
H25C H 0.5497 0.3948 0.1442 0.054 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'
Si Si 0.0817 0.0704 '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
C22 Si1 C21 110.01(10) . . ?
C22 Si1 C1 106.36(9) . . ?
C21 Si1 C1 109.08(9) . . ?
C22 Si1 C23 111.15(10) . . ?
C21 Si1 C23 111.12(10) . . ?
C1 Si1 C23 108.98(9) . . ?
C12 Si2 C11 108.96(10) . . ?
C12 Si2 C4 105.32(9) . . ?
C11 Si2 C4 114.26(9) . . ?
C12 Si2 C13 110.60(9) . . ?
C11 Si2 C13 109.75(9) . . ?
C4 Si2 C13 107.85(9) . . ?
C1 C2 C7 131.91(17) . 2_666 ?
C1 C2 C3 108.05(16) . . ?
C7 C2 C3 120.05(16) 2_666 . ?
C1 O1 C4 110.69(14) . . ?
O1 C4 C3 106.83(15) . . ?
O1 C4 Si2 109.55(12) . . ?
C3 C4 Si2 143.18(14) . . ?
C4 C3 C2 106.96(16) . . ?
C4 C3 C5 133.20(17) . . ?
C2 C3 C5 119.80(16) . . ?
C2 C1 O1 107.46(15) . . ?
C2 C1 Si1 137.95(14) . . ?
O1 C1 Si1 114.51(13) . . ?
C6 C7 C2 118.82(17) . 2_666 ?
C6 C7 H7 120.6 . . ?
C2 C7 H7 120.6 2_666 . ?
C7 C6 C5 122.92(17) . . ?
C7 C6 H6 118.5 . . ?
C5 C6 H6 118.5 . . ?
C5 C5 C6 120.3(2) 2_666 . ?
C5 C5 C3 118.0(2) 2_666 . ?
C6 C5 C3 121.63(16) . . ?
C14 C13 C15 109.00(17) . . ?
C14 C13 C16 108.18(18) . . ?
C15 C13 C16 109.14(17) . . ?
C14 C13 Si2 110.65(14) . . ?
C15 C13 Si2 109.65(14) . . ?
C16 C13 Si2 110.19(14) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
Si2 C11 H11A 109.5 . . ?
Si2 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
Si2 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
Si2 C12 H12A 109.5 . . ?
Si2 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
Si2 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
Si1 C21 H21A 109.5 . . ?
Si1 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
Si1 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C25 C23 C24 109.17(18) . . ?
C25 C23 C26 108.91(18) . . ?
C24 C23 C26 108.50(17) . . ?
C25 C23 Si1 109.80(14) . . ?
C24 C23 Si1 109.97(14) . . ?
C26 C23 Si1 110.45(14) . . ?
C23 C26 H26A 109.5 . . ?
C23 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C23 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
Si1 C22 H22A 109.5 . . ?
Si1 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
Si1 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C23 C25 H25A 109.5 . . ?
C23 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C23 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
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
Si1 C22 1.859(2) . ?
Si1 C21 1.861(2) . ?
Si1 C1 1.8722(19) . ?
Si1 C23 1.889(2) . ?
Si2 C12 1.865(2) . ?
Si2 C11 1.865(2) . ?
Si2 C4 1.8846(19) . ?
Si2 C13 1.890(2) . ?
C2 C1 1.368(3) . ?
C2 C7 1.426(3) 2_666 ?
C2 C3 1.442(2) . ?
O1 C1 1.374(2) . ?
O1 C4 1.387(2) . ?
C4 C3 1.387(3) . ?
C3 C5 1.443(2) . ?
C7 C6 1.345(3) . ?
C7 C2 1.426(3) 2_666 ?
C7 H7 0.9500 . ?
C6 C5 1.439(3) . ?
C6 H6 0.9500 . ?
C5 C5 1.393(4) 2_666 ?
C13 C14 1.529(3) . ?
C13 C15 1.531(3) . ?
C13 C16 1.535(3) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C23 C25 1.527(3) . ?
C23 C24 1.529(3) . ?
C23 C26 1.535(3) . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
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_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4 C3 C5 C6 -0.8(3) . . . . ?
C7 C6 C5 C3 -179.18(18) . . . . ?
