#------------------------------------------------------------------------------
#$Date: 2025-08-19 22:06:29 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301812 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/34/4023471.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_4023471
loop_
_publ_author_name
'Masahiko Shibahara'
'Motonori Watanabe'
'Tetsuo Iwanaga'
'Taisuke Matsumoto'
'Keiko Ideta'
'Teruo Shinmyozu'
_publ_contact_author_address
;
    Department of Chemistry, Faculty of Education and Welfare Science,
    Oita University, Dan-noharu 700, Oita 870-1192, Japan
;
_publ_contact_author_email       mshiba@cc.oita-u.ac.jp
_publ_contact_author_fax         '+81 97 554 7553'
_publ_contact_author_name        ' Masahiko Shibahara'
_publ_contact_author_phone       '+81 97 554 7553'
_publ_section_title
;
 Synthesis, Structure, and Transannular π-π Interaction of
 Three- and Four-Layered [3.3]Paracyclophanes
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4433
_journal_page_last               4442
_journal_paper_doi               10.1021/jo8003309
_journal_volume                  73
_journal_year                    2008
_chemical_formula_moiety         'C42 H44 O2 '
_chemical_formula_sum            'C42 H44 O2'
_chemical_formula_weight         580.81
_space_group_IT_number           86
_symmetry_cell_setting           tetragonal
_symmetry_Int_Tables_number      86
_symmetry_space_group_name_Hall  '-P 4bc'
_symmetry_space_group_name_H-M   'P 42/n :2'
_audit_creation_date             'Wed Nov  3 16:36:09 2004'
_audit_creation_method           'by teXsan'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.2667(8)
_cell_length_b                   17.2667(8)
_cell_length_c                   10.1391(4)
_cell_measurement_reflns_used    29431
_cell_measurement_temperature    113.2
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      1.2
_cell_volume                     3022.9(2)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       PROCESS-AUTO
_computing_data_reduction        'teXsan Ver. 1.11'
_computing_publication_material  'teXsan Ver. 1.11'
_computing_structure_refinement  'teXsan Ver. 1.10'
_computing_structure_solution    SIR97
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 1.0000
_diffrn_measured_fraction_theta_max 1.0000
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID Imaging Plate'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.068
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            28356
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_correction_T_min  0.687
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Higashi, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.276
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.190
_refine_diff_density_max         0.52
_refine_diff_density_min         -0.47
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.889
_refine_ls_hydrogen_treatment    noref
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3466
_refine_ls_R_factor_gt           0.0462
_refine_ls_shift/su_max          0.0002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²) + (0.05000(Max(Fo²,0) + 2Fc²)/3)²]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1234
_reflns_number_gt                1932
_reflns_number_total             3466
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            jo8003309-File007.cif
_cod_data_source_block           4LPCP-Dione
_cod_original_sg_symbol_H-M      'P 42/n'
_cod_original_formula_sum        'C42 H44 O2 '
_cod_database_code               4023471
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
1/2-x,1/2-y,z
-y,1/2+x,1/2+z
1/2+y,-x,1/2+z
-x,-y,-z
1/2+x,1/2+y,-z
y,1/2-x,1/2-z
1/2-y,x,1/2-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_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O(1) O 0.08193(9) 0.06480(10) 0.8983(2) 0.0369(5) Uani 1.00 d . . .
C(1) C 0.0661(1) -0.1549(1) 0.3016(2) 0.0269(6) Uani 1.00 d . . .
C(2) C 0.1435(1) -0.1910(1) 0.2548(2) 0.0320(6) Uani 1.00 d . . .
C(3) C 0.1940(1) -0.1424(1) 0.1622(2) 0.0330(6) Uani 1.00 d . . .
C(4) C 0.2289(1) -0.0711(1) 0.2249(2) 0.0264(6) Uani 1.00 d . . .
C(5) C 0.2213(1) 0.0023(1) 0.1686(2) 0.0278(6) Uani 1.00 d . . .
C(6) C 0.2402(1) 0.0684(1) 0.2404(2) 0.0271(6) Uani 1.00 d . . .
C(7) C 0.2679(1) 0.0637(1) 0.3681(2) 0.0242(6) Uani 1.00 d . . .
C(8) C 0.2852(1) -0.0099(1) 0.4169(2) 0.0252(6) Uani 1.00 d . . .
C(9) C 0.2660(1) -0.0758(1) 0.3473(2) 0.0266(6) Uani 1.00 d . . .
C(10) C 0.2747(1) 0.1349(1) 0.4558(2) 0.0284(6) Uani 1.00 d . . .
C(11) C 0.2344(1) 0.1279(1) 0.5905(2) 0.0286(6) Uani 1.00 d . . .
C(12) C 0.1449(1) 0.1252(1) 0.5898(2) 0.0264(6) Uani 1.00 d . . .
C(13) C 0.1121(1) 0.0528(1) 0.5270(2) 0.0208(5) Uani 1.00 d . . .
C(14) C 0.0829(1) 0.0570(1) 0.3998(2) 0.0214(5) Uani 1.00 d . . .
C(15) C 0.0607(1) -0.0079(1) 0.3281(2) 0.0211(5) Uani 1.00 d . . .
C(16) C 0.0742(1) -0.0814(1) 0.3814(2) 0.0215(5) Uani 1.00 d . . .
C(17) C 0.0955(1) -0.0853(1) 0.5141(2) 0.0206(5) Uani 1.00 d . . .
C(18) C 0.1108(1) -0.0197(1) 0.5890(2) 0.0199(5) Uani 1.00 d . . .
C(19) C 0.1218(1) -0.0267(1) 0.7378(2) 0.0245(6) Uani 1.00 d . . .
C(20) C 0.0614(1) 0.0164(1) 0.8186(2) 0.0241(6) Uani 1.00 d . . .
C(21) C -0.0242(1) -0.0044(1) 0.8068(2) 0.0263(6) Uani 1.00 d . . .
H(1) H 0.0388 -0.1978 0.3659 0.0348 Uiso 1.00 calc . . .
H(2) H 0.0353 -0.1464 0.2206 0.0348 Uiso 1.00 calc . . .
H(3) H 0.1747 -0.2047 0.3393 0.0348 Uiso 1.00 calc . . .
H(4) H 0.1277 -0.2423 0.2140 0.0348 Uiso 1.00 calc . . .
H(5) H 0.1633 -0.1282 0.0766 0.0348 Uiso 1.00 calc . . .
H(6) H 0.2369 -0.1754 0.1289 0.0348 Uiso 1.00 calc . . .
H(7) H 0.2007 0.0106 0.0759 0.0348 Uiso 1.00 calc . . .
H(8) H 0.2336 0.1158 0.1896 0.0348 Uiso 1.00 calc . . .
H(9) H 0.3133 -0.0167 0.4999 0.0348 Uiso 1.00 calc . . .
H(10) H 0.2641 -0.1332 0.3978 0.0348 Uiso 1.00 calc . . .
H(11) H 0.2447 0.1768 0.4018 0.0348 Uiso 1.00 calc . . .
H(12) H 0.3326 0.1486 0.4709 0.0348 Uiso 1.00 calc . . .
H(13) H 0.2559 0.1806 0.6301 0.0348 Uiso 1.00 calc . . .
H(14) H 0.2579 0.0808 0.6385 0.0348 Uiso 1.00 calc . . .
H(15) H 0.1274 0.1750 0.5355 0.0348 Uiso 1.00 calc . . .
H(16) H 0.1313 0.1317 0.6824 0.0348 Uiso 1.00 calc . . .
H(17) H 0.0781 0.1105 0.3644 0.0348 Uiso 1.00 calc . . .
H(18) H 0.0976 -0.1378 0.5565 0.0348 Uiso 1.00 calc . . .
H(19) H 0.1815 -0.0067 0.7537 0.0348 Uiso 1.00 calc . . .
H(20) H 0.1250 -0.0871 0.7600 0.0348 Uiso 1.00 calc . . .
H(21) H -0.0316 -0.0592 0.8327 0.0348 Uiso 1.00 calc . . .
H(22) H -0.0536 0.0226 0.8766 0.0348 Uiso 1.00 calc . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.003 0.002
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
H H 0.000 0.000
;International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.2)
;
O O 0.011 0.006
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C(2) C(1) C(16) 115.0(2) . . . yes
C(1) C(2) C(3) 117.3(2) . . . yes
C(2) C(3) C(4) 114.6(2) . . . yes
C(3) C(4) C(5) 122.0(2) . . . yes
C(3) C(4) C(9) 120.6(2) . . . yes
C(5) C(4) C(9) 117.3(2) . . . yes
C(4) C(5) C(6) 120.6(2) . . . yes
C(5) C(6) C(7) 121.5(2) . . . yes
C(6) C(7) C(8) 117.3(2) . . . yes
C(6) C(7) C(10) 121.8(2) . . . yes
C(8) C(7) C(10) 120.8(2) . . . yes
C(7) C(8) C(9) 121.2(2) . . . yes
C(4) C(9) C(8) 121.1(2) . . . yes
C(7) C(10) C(11) 114.9(2) . . . yes
C(10) C(11) C(12) 116.8(2) . . . yes
C(11) C(12) C(13) 113.6(2) . . . yes
C(12) C(13) C(14) 119.0(2) . . . yes
C(12) C(13) C(18) 123.8(2) . . . yes
C(14) C(13) C(18) 117.3(2) . . . yes
C(13) C(14) C(15) 123.0(2) . . . yes
C(14) C(15) C(16) 118.9(2) . . . yes
C(14) C(15) C(21) 118.2(2) . . 5_556 yes
C(16) C(15) C(21) 122.9(2) . . 5_556 yes
C(1) C(16) C(15) 122.6(2) . . . yes
C(1) C(16) C(17) 120.0(2) . . . yes
C(15) C(16) C(17) 117.4(2) . . . yes
C(16) C(17) C(18) 122.5(2) . . . yes
C(13) C(18) C(17) 119.1(2) . . . yes
C(13) C(18) C(19) 120.8(2) . . . yes
C(17) C(18) C(19) 120.0(2) . . . yes
C(18) C(19) C(20) 114.1(2) . . . yes
O(1) C(20) C(19) 119.6(2) . . . yes
O(1) C(20) C(21) 119.8(2) . . . yes
C(19) C(20) C(21) 120.4(2) . . . yes
C(15) C(21) C(20) 116.1(2) 5_556 . . yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O(1) C(20) 1.215(3) . . yes
C(1) C(2) 1.550(3) . . yes
C(1) C(16) 1.512(3) . . yes
C(2) C(3) 1.531(3) . . yes
C(3) C(4) 1.511(3) . . yes
C(4) C(5) 1.396(3) . . yes
C(4) C(9) 1.398(3) . . yes
C(5) C(6) 1.393(3) . . yes
C(6) C(7) 1.383(3) . . yes
C(7) C(8) 1.396(3) . . yes
C(7) C(10) 1.522(3) . . yes
C(8) C(9) 1.379(3) . . yes
C(10) C(11) 1.537(3) . . yes
C(11) C(12) 1.546(3) . . yes
C(12) C(13) 1.513(3) . . yes
C(13) C(14) 1.386(3) . . yes
C(13) C(18) 1.402(3) . . yes
C(14) C(15) 1.390(3) . . yes
C(15) C(16) 1.399(3) . . yes
C(15) C(21) 1.521(3) . 5_556 yes
C(16) C(17) 1.396(3) . . yes
C(17) C(18) 1.389(3) . . yes
C(18) C(19) 1.525(3) . . yes
C(19) C(20) 1.521(3) . . yes
C(20) C(21) 1.525(3) . . yes
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
O(1) C(10) 3.272(3) . 7_556 ?
O(1) C(21) 3.320(3) . 5_557 ?
O(1) C(11) 3.558(3) . 7_556 ?
O(1) C(8) 3.569(3) . 7_556 ?
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
O(1) C(20) C(19) C(18) -123.5(2) . . . . yes
O(1) C(20) C(21) C(15) 121.3(2) . . . 5_556 yes
C(1) C(2) C(3) C(4) 68.0(3) . . . . yes
C(1) C(16) C(15) C(14) -168.3(2) . . . . yes
C(1) C(16) C(15) C(21) 10.4(3) . . . 5_556 yes
C(1) C(16) C(17) C(18) 173.9(2) . . . . yes
C(2) C(1) C(16) C(15) 102.3(2) . . . . yes
C(2) C(1) C(16) C(17) -78.1(2) . . . . yes
C(2) C(3) C(4) C(5) -127.8(2) . . . . yes
C(2) C(3) C(4) C(9) 47.7(3) . . . . yes
C(3) C(2) C(1) C(16) -62.0(3) . . . . yes
C(3) C(4) C(5) C(6) 167.1(2) . . . . yes
C(3) C(4) C(9) C(8) -167.7(2) . . . . yes
C(4) C(5) C(6) C(7) 0.8(3) . . . . yes
C(4) C(9) C(8) C(7) 0.4(3) . . . . yes
C(5) C(4) C(9) C(8) 8.1(3) . . . . yes
C(5) C(6) C(7) C(8) 7.6(3) . . . . yes
C(5) C(6) C(7) C(10) -168.5(2) . . . . yes
C(6) C(5) C(4) C(9) -8.6(3) . . . . yes
C(6) C(7) C(8) C(9) -8.2(3) . . . . yes
C(6) C(7) C(10) C(11) 126.5(2) . . . . yes
C(7) C(10) C(11) C(12) -68.8(2) . . . . yes
C(8) C(7) C(10) C(11) -49.6(3) . . . . yes
C(9) C(8) C(7) C(10) 168.0(2) . . . . yes
C(10) C(11) C(12) C(13) 66.9(2) . . . . yes
C(11) C(12) C(13) C(14) -102.4(2) . . . . yes
C(11) C(12) C(13) C(18) 76.2(2) . . . . yes
C(12) C(13) C(14) C(15) 171.6(2) . . . . yes
C(12) C(13) C(18) C(17) -166.0(2) . . . . yes
C(12) C(13) C(18) C(19) 17.2(3) . . . . yes
C(13) C(14) C(15) C(16) -5.5(3) . . . . yes
C(13) C(14) C(15) C(21) 175.7(2) . . . 5_556 yes
C(13) C(18) C(17) C(16) -6.1(3) . . . . yes
C(13) C(18) C(19) C(20) 59.8(3) . . . . yes
C(14) C(13) C(18) C(17) 12.6(3) . . . . yes
C(14) C(13) C(18) C(19) -164.2(2) . . . . yes
C(14) C(15) C(16) C(17) 12.1(3) . . . . yes
C(14) C(15) C(21) C(20) -111.5(2) . . 5_556 5_556 yes
C(15) C(14) C(13) C(18) -7.0(3) . . . . yes
C(15) C(16) C(17) C(18) -6.5(3) . . . . yes
C(15) C(21) C(20) C(19) 62.8(3) . 5_556 5_556 5_556 yes
C(16) C(15) C(21) C(20) 69.8(3) . . 5_556 5_556 yes
C(16) C(17) C(18) C(19) 170.7(2) . . . . yes
C(17) C(16) C(15) C(21) -169.3(2) . . . 5_556 yes
C(17) C(18) C(19) C(20) -117.0(2) . . . . yes
C(18) C(19) C(20) C(21) 60.6(2) . . . . yes
C(18) C(19) C(20) C(21) 60.6(2) . . . . yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 102405829
