#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/27/4022706.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_4022706
loop_
_publ_author_name
'Masahiko Shibahara'
'Motonori Watanabe'
'Tetsuo Iwanaga'
'Keiko Ideta'
'Teruo Shinmyozu'
_publ_section_title
;
 Synthesis, Structure, and Transannular π-π Interaction
 of Multilayered [3.3]Metacyclophanes
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2865
_journal_page_last               2877
_journal_paper_doi               10.1021/jo062220m
_journal_volume                  72
_journal_year                    2007
_chemical_formula_moiety         'C30 H34 '
_chemical_formula_sum            'C30 H34'
_chemical_formula_weight         394.60
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yab'
_symmetry_space_group_name_H-M   'P 1 21/a 1'
_audit_creation_date             'Tue Oct  5 11:13:34 2004'
_audit_creation_method           'by teXsan'
_cell_angle_alpha                90
_cell_angle_beta                 112.8119(8)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.8209(3)
_cell_length_b                   16.5040(7)
_cell_length_c                   9.1190(3)
_cell_measurement_reflns_used    10173
_cell_measurement_temperature    113.2
_cell_measurement_theta_max      27.4
_cell_measurement_theta_min      2.4
_cell_volume                     1084.98(7)
_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 0.9911
_diffrn_measured_fraction_theta_max 0.9911
_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  0.026
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            9425
_diffrn_reflns_theta_full        27.38
_diffrn_reflns_theta_max         27.38
_exptl_absorpt_coefficient_mu    0.067
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_correction_T_min  0.761
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Higashi, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.208
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_size_max          0.460
_exptl_crystal_size_mid          0.430
_exptl_crystal_size_min          0.210
_refine_diff_density_max         0.18
_refine_diff_density_min         -0.17
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.682
_refine_ls_hydrogen_treatment    noref
_refine_ls_number_parameters     136
_refine_ls_number_reflns         2445
_refine_ls_R_factor_gt           0.0435
_refine_ls_shift/su_max          0.0003
_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         0.1235
_reflns_number_gt                2088
_reflns_number_total             2445
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            jo062220msi20061026_030156.cif
_cod_data_source_block           a
_cod_original_sg_symbol_H-M      'P 21/a'
_cod_original_formula_sum        'C30 H34 '
_cod_database_code               4022706
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
1/2-x,1/2+y,-z
-x,-y,-z
1/2+x,1/2-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_calc_flag
C(1) C 0.4452(1) 0.07786(6) 0.5033(1) 0.0160(3) Uani 1.00 d
C(2) C 0.3873(1) 0.03883(7) 0.3561(1) 0.0154(3) Uani 1.00 d
C(3) C 0.2724(2) 0.08535(7) 0.2067(1) 0.0211(3) Uani 1.00 d
C(4) C 0.3735(2) 0.11363(7) 0.1003(1) 0.0234(3) Uani 1.00 d
C(5) C 0.5038(2) 0.18653(7) 0.1606(1) 0.0229(3) Uani 1.00 d
C(6) C 0.6782(2) 0.16803(6) 0.3050(1) 0.0184(3) Uani 1.00 d
C(7) C 0.8127(2) 0.11598(7) 0.2926(1) 0.0204(3) Uani 1.00 d
C(8) C 0.9649(2) 0.09397(7) 0.4271(1) 0.0218(3) Uani 1.00 d
C(9) C 0.9817(2) 0.12137(7) 0.5757(1) 0.0211(3) Uani 1.00 d
C(10) C 0.8489(2) 0.17281(6) 0.5918(1) 0.0188(3) Uani 1.00 d
C(11) C 0.7023(2) 0.19816(6) 0.4539(1) 0.0184(3) Uani 1.00 d
C(12) C 0.8564(2) 0.19652(7) 0.7541(1) 0.0234(3) Uani 1.00 d
C(13) C 0.8258(2) 0.12579(7) 0.8512(1) 0.0232(3) Uani 1.00 d
C(14) C 0.6263(2) 0.09246(7) 0.7970(1) 0.0208(3) Uani 1.00 d
C(15) C 0.5592(1) 0.04213(6) 0.6464(1) 0.0158(3) Uani 1.00 d
H(1) H 0.4038 0.1330 0.5056 0.0310 Uiso 1.00 calc
H(2) H 0.2201 0.1309 0.2254 0.0310 Uiso 1.00 calc
H(3) H 0.1714 0.0540 0.1438 0.0310 Uiso 1.00 calc
H(4) H 0.2780 0.1266 -0.0065 0.0310 Uiso 1.00 calc
H(5) H 0.4339 0.0684 0.0740 0.0310 Uiso 1.00 calc
H(6) H 0.5372 0.2062 0.0726 0.0310 Uiso 1.00 calc
H(7) H 0.4263 0.2327 0.1745 0.0310 Uiso 1.00 calc
H(8) H 0.7914 0.0892 0.1893 0.0310 Uiso 1.00 calc
H(9) H 1.0471 0.0591 0.4107 0.0310 Uiso 1.00 calc
H(10) H 1.0801 0.1053 0.6727 0.0310 Uiso 1.00 calc
H(11) H 0.6182 0.2370 0.4663 0.0310 Uiso 1.00 calc
H(12) H 0.7570 0.2409 0.7420 0.0310 Uiso 1.00 calc
H(13) H 0.9675 0.2189 0.8080 0.0310 Uiso 1.00 calc
H(14) H 0.9156 0.0811 0.8559 0.0310 Uiso 1.00 calc
H(15) H 0.8720 0.1430 0.9672 0.0310 Uiso 1.00 calc
H(16) H 0.6225 0.0604 0.8897 0.0310 Uiso 1.00 calc
H(17) H 0.5526 0.1348 0.7929 0.0310 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)
;
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
C(2) C(1) C(15) 123.77(10) . . yes
C(1) C(2) C(3) 119.22(10) . . yes
C(1) C(2) C(15) 117.86(10) . 3_656 yes
C(3) C(2) C(15) 122.92(10) . 3_656 yes
C(2) C(3) C(4) 116.65(9) . . yes
C(3) C(4) C(5) 116.31(9) . . yes
C(4) C(5) C(6) 113.75(9) . . yes
C(5) C(6) C(7) 120.4(1) . . yes
C(5) C(6) C(11) 120.8(1) . . yes
C(7) C(6) C(11) 118.6(1) . . yes
C(6) C(7) C(8) 120.4(1) . . yes
C(7) C(8) C(9) 120.2(1) . . yes
C(8) C(9) C(10) 120.7(1) . . yes
C(9) C(10) C(11) 118.2(1) . . yes
C(9) C(10) C(12) 120.92(10) . . yes
C(11) C(10) C(12) 120.7(1) . . yes
C(6) C(11) C(10) 121.69(10) . . yes
C(10) C(12) C(13) 114.32(9) . . yes
C(12) C(13) C(14) 116.71(10) . . yes
C(13) C(14) C(15) 115.96(9) . . yes
C(1) C(15) C(2) 118.32(10) . 3_656 yes
C(1) C(15) C(14) 119.20(10) . . yes
C(2) C(15) C(14) 122.45(10) 3_656 . yes
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
C(1) C(2) 1.396(1) . yes
C(1) C(15) 1.394(2) . yes
C(2) C(3) 1.518(1) . yes
C(2) C(15) 1.403(2) 3_656 yes
C(3) C(4) 1.542(2) . yes
C(4) C(5) 1.534(2) . yes
C(5) C(6) 1.515(2) . yes
C(6) C(7) 1.396(2) . yes
C(6) C(11) 1.388(2) . yes
C(7) C(8) 1.386(2) . yes
C(8) C(9) 1.386(2) . yes
C(9) C(10) 1.393(2) . yes
C(10) C(11) 1.398(2) . yes
C(10) C(12) 1.510(2) . yes
C(12) C(13) 1.539(2) . yes
C(13) C(14) 1.544(2) . yes
C(14) C(15) 1.514(1) . yes
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_2
C(1) C(8) 3.556(2) 1_455
C(8) C(8) 3.335(2) 3_756
C(8) C(9) 3.580(2) 3_756
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_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C(1) C(2) C(3) C(4) 104.2(1) . . yes
C(1) C(2) C(15) C(14) 175.07(9) 3_656 3_656 yes
C(1) C(15) C(2) C(3) -176.55(9) 3_656 3_656 yes
C(1) C(15) C(14) C(13) -99.9(1) . . yes
C(2) C(1) C(15) C(14) 174.98(10) . . yes
C(2) C(3) C(4) C(5) -75.3(1) . . yes
C(3) C(2) C(1) C(15) -176.43(9) . . yes
C(3) C(2) C(15) C(14) -5.7(2) 3_656 3_656 yes
C(3) C(4) C(5) C(6) 70.2(1) . . yes
C(4) C(3) C(2) C(15) -75.0(1) . 3_656 yes
C(4) C(5) C(6) C(7) 67.7(1) . . yes
C(4) C(5) C(6) C(11) -108.1(1) . . yes
C(5) C(6) C(7) C(8) -174.80(10) . . yes
C(5) C(6) C(11) C(10) 170.86(10) . . yes
C(6) C(7) C(8) C(9) 2.2(2) . . yes
C(6) C(11) C(10) C(9) 5.6(2) . . yes
C(6) C(11) C(10) C(12) -170.76(10) . . yes
C(7) C(6) C(11) C(10) -5.0(2) . . yes
C(7) C(8) C(9) C(10) -1.6(2) . . yes
C(8) C(7) C(6) C(11) 1.1(2) . . yes
C(8) C(9) C(10) C(11) -2.2(2) . . yes
C(8) C(9) C(10) C(12) 174.15(10) . . yes
C(9) C(10) C(12) C(13) -65.5(1) . . yes
C(10) C(12) C(13) C(14) -72.7(1) . . yes
C(11) C(10) C(12) C(13) 110.8(1) . . yes
C(12) C(13) C(14) C(15) 73.7(1) . . yes
C(12) C(13) C(14) C(15) 73.7(1) . . yes
