#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/40/4024080.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_4024080
loop_
_publ_author_name
'Toshiaki Shimasaki'
'Shin-ichiro Kato'
'Teruo Shinmyozu'
_publ_contact_author_address
;
Institute for Materials Chemistry and Engineering (IMCE),
6-10-1 Higashi-ku, Fukuoka 812-8581, Japan
;
_publ_contact_author_email       shinmyo@ms.ifoc.kyushu-u.ac.jp
_publ_contact_author_fax         '+81 92 642 2735'
_publ_contact_author_name        'Prof Teruo Shinmyozu'
_publ_contact_author_phone       '+81 92 642 2716'
_publ_section_title
;
 Synthesis, Structural, Spectral, and Photoswitchable Properties of
 cis- and trans-2,2,2',2'-Tetramethyl-1,1'-indanylindanes
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6251
_journal_page_last               6254
_journal_paper_doi               10.1021/jo0701233
_journal_volume                  72
_journal_year                    2007
_chemical_formula_moiety         'C22 H22 Br2 '
_chemical_formula_sum            'C22 H22 Br2'
_chemical_formula_weight         446.22
_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
_cell_angle_alpha                104.91
_cell_angle_beta                 108.71
_cell_angle_gamma                110.08
_cell_formula_units_Z            2
_cell_length_a                   8.593
_cell_length_b                   11.344
_cell_length_c                   11.883
_cell_measurement_temperature    113(2)
_cell_volume                     938.4
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      113(2)
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0411
_diffrn_reflns_av_sigmaI/netI    0.0342
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8534
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         1.99
_exptl_absorpt_coefficient_mu    8.639
_exptl_absorpt_correction_T_max  0.4787
_exptl_absorpt_correction_T_min  0.2769
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    3.158
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.857
_refine_diff_density_min         -1.190
_refine_diff_density_rms         0.156
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         4209
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0436
_refine_ls_R_factor_gt           0.0373
_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)+(0.0648P)²+0.6052P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0978
_refine_ls_wR_factor_ref         0.1011
_reflns_number_gt                3728
_reflns_number_total             4209
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo0701233si20070114_063230_4.cif
_cod_data_source_block           cis-2(CCDC:625983)
_cod_original_sg_symbol_H-M      'P -1         '
_cod_original_formula_sum        'C22 H22 Br2 '
_cod_database_code               4024080
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
C1 C -0.2751(3) 0.2874(3) -0.3111(2) 0.0123(5) Uani 1 1 d . . .
C2 C -0.3779(3) 0.3208(3) -0.4223(2) 0.0125(5) Uani 1 1 d . . .
C3 C -0.5442(3) 0.1755(3) -0.5186(2) 0.0136(5) Uani 1 1 d . . .
H1 H -0.6529 0.1831 -0.5713 0.016 Uiso 1 1 calc R . .
H2 H -0.5098 0.1229 -0.5780 0.016 Uiso 1 1 calc R . .
C4 C -0.7510(4) 0.0051(3) -0.4540(3) 0.0146(5) Uani 1 1 d . . .
H3 H -0.8577 -0.0385 -0.5360 0.018 Uiso 1 1 calc R . .
C5 C -0.7548(3) -0.0315(3) -0.3519(3) 0.0139(5) Uani 1 1 d . . .
C6 C -0.6022(4) 0.0306(3) -0.2308(3) 0.0145(5) Uani 1 1 d . . .
H4 H -0.6106 0.0039 -0.1626 0.017 Uiso 1 1 calc R . .
C7 C -0.4357(4) 0.1333(3) -0.2107(2) 0.0137(5) Uani 1 1 d . . .
H22 H -0.3295 0.1772 -0.1283 0.016 Uiso 1 1 calc R . .
C8 C -0.4257(4) 0.1712(3) -0.3124(2) 0.0123(5) Uani 1 1 d . . .
C9 C -0.5847(3) 0.1082(3) -0.4313(2) 0.0132(5) Uani 1 1 d . . .
C10 C -0.2786(4) 0.3728(3) -0.4989(3) 0.0173(5) Uani 1 1 d . . .
H5 H -0.2296 0.3113 -0.5287 0.026 Uiso 1 1 calc R . .
H6 H -0.1761 0.4661 -0.4426 0.026 Uiso 1 1 calc R . .
H7 H -0.3664 0.3745 -0.5745 0.026 Uiso 1 1 calc R . .
C11 C -0.4575(4) 0.4147(3) -0.3731(3) 0.0177(5) Uani 1 1 d . . .
H8 H -0.5201 0.3788 -0.3244 0.027 Uiso 1 1 calc R . .
H9 H -0.5467 0.4167 -0.4477 0.027 Uiso 1 1 calc R . .
H10 H -0.3562 0.5082 -0.3158 0.027 Uiso 1 1 calc R . .
C12 C -0.0911(3) 0.3439(3) -0.2291(2) 0.0120(5) Uani 1 1 d . . .
C13 C 0.0720(4) 0.4852(3) -0.1908(2) 0.0142(5) Uani 1 1 d . . .
C14 C 0.2076(4) 0.5162(3) -0.0506(2) 0.0158(5) Uani 1 1 d . . .
H11 H 0.3381 0.5718 -0.0308 0.019 Uiso 1 1 calc R . .
H12 H 0.1798 0.5659 0.0156 0.019 Uiso 1 1 calc R . .
C15 C 0.2884(4) 0.3396(3) 0.0246(2) 0.0157(5) Uani 1 1 d . . .
H13 H 0.4071 0.4075 0.0932 0.019 Uiso 1 1 calc R . .
C16 C 0.2253(4) 0.2010(3) 0.0004(2) 0.0159(5) Uani 1 1 d . . .
C17 C 0.0523(4) 0.0999(3) -0.1011(3) 0.0163(5) Uani 1 1 d . . .
H14 H 0.0131 0.0055 -0.1172 0.020 Uiso 1 1 calc R . .
C18 C -0.0628(4) 0.1392(3) -0.1788(2) 0.0146(5) Uani 1 1 d . . .
H15 H -0.1809 0.0713 -0.2483 0.018 Uiso 1 1 calc R . .
C19 C -0.0039(3) 0.2777(3) -0.1543(2) 0.0125(5) Uani 1 1 d . . .
C20 C 0.1723(3) 0.3758(3) -0.0547(2) 0.0141(5) Uani 1 1 d . . .
C21 C 0.1692(4) 0.4693(3) -0.2779(3) 0.0193(5) Uani 1 1 d . . .
H16 H 0.1941 0.3906 -0.2820 0.029 Uiso 1 1 calc R . .
H17 H 0.2866 0.5533 -0.2414 0.029 Uiso 1 1 calc R . .
H18 H 0.0890 0.4538 -0.3660 0.029 Uiso 1 1 calc R . .
C22 C 0.0304(4) 0.6068(3) -0.1818(3) 0.0191(5) Uani 1 1 d . . .
H19 H -0.0313 0.6144 -0.1257 0.029 Uiso 1 1 calc R . .
H20 H -0.0510 0.5921 -0.2692 0.029 Uiso 1 1 calc R . .
H21 H 0.1467 0.6918 -0.1446 0.029 Uiso 1 1 calc R . .
Br1 Br -0.98043(3) -0.17224(3) -0.37828(3) 0.01862(10) Uani 1 1 d . . .
Br2 Br 0.37917(4) 0.14636(3) 0.10586(3) 0.02276(10) Uani 1 1 d . . .
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
C12 C1 C8 124.9(2) . . ?
C12 C1 C2 130.9(2) . . ?
C8 C1 C2 104.2(2) . . ?
C10 C2 C11 111.4(2) . . ?
C10 C2 C1 118.6(2) . . ?
C11 C2 C1 110.2(2) . . ?
C10 C2 C3 107.0(2) . . ?
C11 C2 C3 107.7(2) . . ?
C1 C2 C3 100.85(19) . . ?
C9 C3 C2 103.9(2) . . ?
C9 C3 H1 111.0 . . ?
C2 C3 H1 111.0 . . ?
C9 C3 H2 111.0 . . ?
C2 C3 H2 111.0 . . ?
H1 C3 H2 109.0 . . ?
C5 C4 C9 117.2(2) . . ?
C5 C4 H3 121.4 . . ?
C9 C4 H3 121.4 . . ?
C6 C5 C4 122.9(2) . . ?
C6 C5 Br1 118.39(19) . . ?
C4 C5 Br1 118.68(19) . . ?
C5 C6 C7 118.8(2) . . ?
C5 C6 H4 120.6 . . ?
C7 C6 H4 120.6 . . ?
C6 C7 C8 119.8(2) . . ?
C6 C7 H22 120.1 . . ?
C8 C7 H22 120.1 . . ?
C9 C8 C7 119.1(2) . . ?
C9 C8 C1 110.3(2) . . ?
C7 C8 C1 130.0(2) . . ?
C4 C9 C8 122.1(2) . . ?
C4 C9 C3 128.8(2) . . ?
C8 C9 C3 109.0(2) . . ?
C2 C10 H5 109.5 . . ?
C2 C10 H6 109.5 . . ?
H5 C10 H6 109.5 . . ?
C2 C10 H7 109.5 . . ?
H5 C10 H7 109.5 . . ?
H6 C10 H7 109.5 . . ?
C2 C11 H8 109.5 . . ?
C2 C11 H9 109.5 . . ?
H8 C11 H9 109.5 . . ?
C2 C11 H10 109.5 . . ?
H8 C11 H10 109.5 . . ?
H9 C11 H10 109.5 . . ?
C1 C12 C19 125.2(2) . . ?
C1 C12 C13 130.1(2) . . ?
C19 C12 C13 104.7(2) . . ?
C22 C13 C21 111.3(2) . . ?
C22 C13 C12 117.4(2) . . ?
C21 C13 C12 110.3(2) . . ?
C22 C13 C14 107.5(2) . . ?
C21 C13 C14 107.8(2) . . ?
C12 C13 C14 101.8(2) . . ?
C20 C14 C13 103.6(2) . . ?
C20 C14 H11 111.0 . . ?
C13 C14 H11 111.0 . . ?
C20 C14 H12 111.0 . . ?
C13 C14 H12 111.0 . . ?
H11 C14 H12 109.0 . . ?
C20 C15 C16 117.9(2) . . ?
C20 C15 H13 121.0 . . ?
C16 C15 H13 121.0 . . ?
C15 C16 C17 121.7(2) . . ?
C15 C16 Br2 119.46(19) . . ?
C17 C16 Br2 118.8(2) . . ?
C16 C17 C18 119.2(2) . . ?
C16 C17 H14 120.4 . . ?
C18 C17 H14 120.4 . . ?
C19 C18 C17 119.9(2) . . ?
C19 C18 H15 120.1 . . ?
C17 C18 H15 120.1 . . ?
C18 C19 C20 119.4(2) . . ?
C18 C19 C12 130.1(2) . . ?
C20 C19 C12 110.0(2) . . ?
C15 C20 C19 121.7(2) . . ?
C15 C20 C14 128.5(2) . . ?
C19 C20 C14 109.8(2) . . ?
C13 C21 H16 109.5 . . ?
C13 C21 H17 109.5 . . ?
H16 C21 H17 109.5 . . ?
C13 C21 H18 109.5 . . ?
H16 C21 H18 109.5 . . ?
H17 C21 H18 109.5 . . ?
C13 C22 H19 109.5 . . ?
C13 C22 H20 109.5 . . ?
H19 C22 H20 109.5 . . ?
C13 C22 H21 109.5 . . ?
H19 C22 H21 109.5 . . ?
H20 C22 H21 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
C1 C12 1.362(4) . ?
C1 C8 1.489(3) . ?
C1 C2 1.552(3) . ?
C2 C10 1.528(3) . ?
C2 C11 1.543(4) . ?
C2 C3 1.559(4) . ?
C3 C9 1.495(3) . ?
C3 H1 0.9900 . ?
C3 H2 0.9900 . ?
C4 C5 1.386(4) . ?
C4 C9 1.387(4) . ?
C4 H3 0.9500 . ?
C5 C6 1.385(4) . ?
C5 Br1 1.906(3) . ?
C6 C7 1.398(4) . ?
C6 H4 0.9500 . ?
C7 C8 1.401(3) . ?
C7 H22 0.9500 . ?
C8 C9 1.395(3) . ?
C10 H5 0.9800 . ?
C10 H6 0.9800 . ?
C10 H7 0.9800 . ?
C11 H8 0.9800 . ?
C11 H9 0.9800 . ?
C11 H10 0.9800 . ?
C12 C19 1.489(3) . ?
C12 C13 1.554(3) . ?
C13 C22 1.525(4) . ?
C13 C21 1.539(4) . ?
C13 C14 1.558(3) . ?
C14 C20 1.500(4) . ?
C14 H11 0.9900 . ?
C14 H12 0.9900 . ?
C15 C20 1.389(4) . ?
C15 C16 1.390(4) . ?
C15 H13 0.9500 . ?
C16 C17 1.395(4) . ?
C16 Br2 1.898(3) . ?
C17 C18 1.400(4) . ?
C17 H14 0.9500 . ?
C18 C19 1.391(4) . ?
C18 H15 0.9500 . ?
C19 C20 1.395(4) . ?
C21 H16 0.9800 . ?
C21 H17 0.9800 . ?
C21 H18 0.9800 . ?
C22 H19 0.9800 . ?
C22 H20 0.9800 . ?
C22 H21 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
C12 C1 C2 C10 31.3(4) . . . . ?
C8 C1 C2 C10 -147.5(2) . . . . ?
C12 C1 C2 C11 -98.8(3) . . . . ?
C8 C1 C2 C11 82.5(2) . . . . ?
C12 C1 C2 C3 147.6(3) . . . . ?
C8 C1 C2 C3 -31.2(2) . . . . ?
C10 C2 C3 C9 157.5(2) . . . . ?
C11 C2 C3 C9 -82.6(2) . . . . ?
C1 C2 C3 C9 32.9(2) . . . . ?
C9 C4 C5 C6 0.4(4) . . . . ?
C9 C4 C5 Br1 179.80(19) . . . . ?
C4 C5 C6 C7 -1.1(4) . . . . ?
Br1 C5 C6 C7 179.57(19) . . . . ?
C5 C6 C7 C8 -0.1(4) . . . . ?
C6 C7 C8 C9 1.9(4) . . . . ?
C6 C7 C8 C1 171.4(2) . . . . ?
C12 C1 C8 C9 -160.1(2) . . . . ?
C2 C1 C8 C9 18.8(3) . . . . ?
C12 C1 C8 C7 29.7(4) . . . . ?
C2 C1 C8 C7 -151.5(3) . . . . ?
C5 C4 C9 C8 1.4(4) . . . . ?
C5 C4 C9 C3 -174.8(3) . . . . ?
C7 C8 C9 C4 -2.6(4) . . . . ?
C1 C8 C9 C4 -174.0(2) . . . . ?
C7 C8 C9 C3 174.4(2) . . . . ?
C1 C8 C9 C3 2.9(3) . . . . ?
C2 C3 C9 C4 153.4(3) . . . . ?
C2 C3 C9 C8 -23.2(3) . . . . ?
C8 C1 C12 C19 18.0(4) . . . . ?
C2 C1 C12 C19 -160.6(2) . . . . ?
C8 C1 C12 C13 -161.7(2) . . . . ?
C2 C1 C12 C13 19.8(4) . . . . ?
C1 C12 C13 C22 34.2(4) . . . . ?
C19 C12 C13 C22 -145.5(2) . . . . ?
C1 C12 C13 C21 -94.7(3) . . . . ?
C19 C12 C13 C21 85.6(2) . . . . ?
C1 C12 C13 C14 151.2(3) . . . . ?
C19 C12 C13 C14 -28.5(2) . . . . ?
C22 C13 C14 C20 154.6(2) . . . . ?
C21 C13 C14 C20 -85.4(2) . . . . ?
C12 C13 C14 C20 30.7(2) . . . . ?
C20 C15 C16 C17 0.9(4) . . . . ?
C20 C15 C16 Br2 179.88(19) . . . . ?
C15 C16 C17 C18 -1.4(4) . . . . ?
Br2 C16 C17 C18 179.54(19) . . . . ?
C16 C17 C18 C19 0.0(4) . . . . ?
C17 C18 C19 C20 2.0(4) . . . . ?
C17 C18 C19 C12 173.7(2) . . . . ?
C1 C12 C19 C18 24.1(4) . . . . ?
C13 C12 C19 C18 -156.2(3) . . . . ?
C1 C12 C19 C20 -163.7(2) . . . . ?
C13 C12 C19 C20 16.0(3) . . . . ?
C16 C15 C20 C19 1.2(4) . . . . ?
C16 C15 C20 C14 -179.0(2) . . . . ?
C18 C19 C20 C15 -2.7(4) . . . . ?
C12 C19 C20 C15 -175.9(2) . . . . ?
C18 C19 C20 C14 177.5(2) . . . . ?
C12 C19 C20 C14 4.3(3) . . . . ?
C13 C14 C20 C15 157.5(3) . . . . ?
C13 C14 C20 C19 -22.7(3) . . . . ?
