#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/86/2228631.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_2228631
loop_
_publ_author_name
'Yao, Min'
'Ding, Yanfeng'
'Wang, Zi-jia'
'Deng, Yuheng'
_publ_section_title
;
 4,4'-Dibromo-7,7'-dimethoxy-1,1'-spirobiindane
;
_journal_coeditor_code           ZQ2071
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3191
_journal_paper_doi               10.1107/S1600536810046519
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C19 H18 Br2 O2'
_chemical_formula_moiety         'C19 H18 Br2 O2'
_chemical_formula_sum            'C19 H18 Br2 O2'
_chemical_formula_weight         438.15
_chemical_name_systematic
;
4,4'-Dibromo-7,7'-dimethoxy-1,1'-spirobiindane
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_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           SHELXL97
_cell_angle_alpha                112.047(2)
_cell_angle_beta                 105.559(2)
_cell_angle_gamma                94.280(2)
_cell_formula_units_Z            2
_cell_length_a                   8.3487(3)
_cell_length_b                   10.4831(3)
_cell_length_c                   11.6293(4)
_cell_measurement_reflns_used    9917
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.0
_cell_measurement_theta_min      2.2
_cell_volume                     891.11(5)
_computing_cell_refinement       'APEX2 and SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
;
SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_diffrn_measurement_method       ω
_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  0.0164
_diffrn_reflns_av_sigmaI/netI    0.0169
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            9917
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         2.24
_exptl_absorpt_coefficient_mu    4.555
_exptl_absorpt_correction_T_max  0.659
_exptl_absorpt_correction_T_min  0.263
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2007)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.633
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             436
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.509
_refine_diff_density_min         -0.406
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3090
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0421
_refine_ls_R_factor_gt           0.0302
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0381P)²+0.4917P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0749
_refine_ls_wR_factor_ref         0.0813
_reflns_number_gt                2470
_reflns_number_total             3090
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            zq2071.cif
_cod_data_source_block           I
_cod_database_code               2228631
_cod_database_fobs_code          2228631
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br1 1.10416(5) -0.01254(4) 0.77083(5) 0.08981(17) Uani d . 1 . .
Br Br2 0.47345(5) 0.80256(3) 0.72566(4) 0.07264(15) Uani d . 1 . .
O O1 0.5993(3) 0.3495(2) 0.9166(2) 0.0653(6) Uani d . 1 . .
O O2 0.4765(2) 0.18707(19) 0.5868(2) 0.0529(5) Uani d . 1 . .
C C1 0.9460(4) 0.1024(3) 0.8190(3) 0.0584(8) Uani d . 1 . .
C C2 0.8577(4) 0.0773(3) 0.8944(3) 0.0627(9) Uani d . 1 . .
H H2A 0.8767 0.0061 0.9227 0.075 Uiso calc R 1 . .
C C3 0.7404(4) 0.1577(3) 0.9285(3) 0.0578(8) Uani d . 1 . .
H H3A 0.6811 0.1406 0.9802 0.069 Uiso calc R 1 . .
C C4 0.7105(4) 0.2636(3) 0.8863(3) 0.0502(7) Uani d . 1 . .
C C5 0.7982(3) 0.2868(3) 0.8074(3) 0.0442(6) Uani d . 1 . .
C C6 0.9173(3) 0.2067(3) 0.7741(3) 0.0503(7) Uani d . 1 . .
C C7 0.9965(4) 0.2507(4) 0.6906(4) 0.0648(9) Uani d . 1 . .
H H7A 1.0008 0.1700 0.6160 0.078 Uiso calc R 1 . .
H H7B 1.1103 0.3053 0.7403 0.078 Uiso calc R 1 . .
C C8 0.8773(4) 0.3406(4) 0.6466(3) 0.0584(8) Uani d . 1 . .
H H8A 0.7945 0.2843 0.5614 0.070 Uiso calc R 1 . .
H H8B 0.9414 0.4179 0.6410 0.070 Uiso calc R 1 . .
C C9 0.7877(3) 0.3968(3) 0.7517(3) 0.0453(6) Uani d . 1 . .
C C10 0.8785(4) 0.5453(3) 0.8581(3) 0.0596(8) Uani d . 1 . .
H H10A 0.8676 0.5560 0.9420 0.072 Uiso calc R 1 . .
H H10B 0.9981 0.5610 0.8671 0.072 Uiso calc R 1 . .
C C11 0.7909(4) 0.6495(3) 0.8117(3) 0.0605(8) Uani d . 1 . .
H H11A 0.7849 0.7308 0.8851 0.073 Uiso calc R 1 . .
H H11B 0.8498 0.6804 0.7625 0.073 Uiso calc R 1 . .
C C12 0.6173(4) 0.5641(3) 0.7261(3) 0.0446(6) Uani d . 1 . .
C C13 0.4707(4) 0.6077(3) 0.6789(3) 0.0477(7) Uani d . 1 . .
C C14 0.3237(4) 0.5120(3) 0.6013(3) 0.0533(7) Uani d . 1 . .
H H14A 0.2257 0.5423 0.5707 0.064 Uiso calc R 1 . .
C C15 0.3202(4) 0.3699(3) 0.5681(3) 0.0498(7) Uani d . 1 . .
H H15A 0.2200 0.3052 0.5150 0.060 Uiso calc R 1 . .
C C16 0.4663(3) 0.3244(3) 0.6142(3) 0.0420(6) Uani d . 1 . .
C C17 0.6141(3) 0.4225(3) 0.6941(2) 0.0394(6) Uani d . 1 . .
C C18 0.5014(7) 0.3249(5) 0.9914(6) 0.1131(17) Uani d . 1 . .
H H18A 0.4297 0.3928 1.0065 0.170 Uiso calc R 1 . .
H H18B 0.5755 0.3330 1.0738 0.170 Uiso calc R 1 . .
H H18C 0.4326 0.2322 0.9444 0.170 Uiso calc R 1 . .
C C19 0.3276(4) 0.0840(3) 0.5120(4) 0.0867(13) Uani d . 1 . .
H H19A 0.3532 -0.0069 0.5001 0.130 Uiso calc R 1 . .
H H19B 0.2833 0.0871 0.4281 0.130 Uiso calc R 1 . .
H H19C 0.2449 0.1017 0.5568 0.130 Uiso calc R 1 . .
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'
Br Br -0.2901 2.4595 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C4 O1 C18 . . 117.9(3) ?
C16 O2 C19 . . 118.4(2) ?
C2 C1 C6 . . 120.7(3) ?
C2 C1 Br1 . . 119.1(2) ?
C6 C1 Br1 . . 120.1(3) ?
C1 C2 C3 . . 120.1(3) ?
C1 C2 H2A . . 120.0 ?
C3 C2 H2A . . 120.0 ?
C2 C3 C4 . . 120.4(3) ?
C2 C3 H3A . . 119.8 ?
C4 C3 H3A . . 119.8 ?
O1 C4 C3 . . 124.6(3) ?
O1 C4 C5 . . 116.1(2) ?
C3 C4 C5 . . 119.3(3) ?
C6 C5 C4 . . 120.2(2) ?
C6 C5 C9 . . 111.3(2) ?
C4 C5 C9 . . 128.4(3) ?
C1 C6 C5 . . 119.2(3) ?
C1 C6 C7 . . 129.8(3) ?
C5 C6 C7 . . 111.0(2) ?
C6 C7 C8 . . 103.2(2) ?
C6 C7 H7A . . 111.1 ?
C8 C7 H7A . . 111.1 ?
C6 C7 H7B . . 111.1 ?
C8 C7 H7B . . 111.1 ?
H7A C7 H7B . . 109.1 ?
C7 C8 C9 . . 106.4(2) ?
C7 C8 H8A . . 110.5 ?
C9 C8 H8A . . 110.5 ?
C7 C8 H8B . . 110.5 ?
C9 C8 H8B . . 110.5 ?
H8A C8 H8B . . 108.6 ?
C17 C9 C5 . . 118.2(2) ?
C17 C9 C10 . . 101.5(2) ?
C5 C9 C10 . . 111.8(2) ?
C17 C9 C8 . . 111.6(2) ?
C5 C9 C8 . . 101.4(2) ?
C10 C9 C8 . . 112.7(2) ?
C11 C10 C9 . . 106.1(2) ?
C11 C10 H10A . . 110.5 ?
C9 C10 H10A . . 110.5 ?
C11 C10 H10B . . 110.5 ?
C9 C10 H10B . . 110.5 ?
H10A C10 H10B . . 108.7 ?
C12 C11 C10 . . 102.8(2) ?
C12 C11 H11A . . 111.2 ?
C10 C11 H11A . . 111.2 ?
C12 C11 H11B . . 111.2 ?
C10 C11 H11B . . 111.2 ?
H11A C11 H11B . . 109.1 ?
C17 C12 C13 . . 119.5(3) ?
C17 C12 C11 . . 110.9(2) ?
C13 C12 C11 . . 129.6(3) ?
C14 C13 C12 . . 120.5(2) ?
C14 C13 Br2 . . 119.9(2) ?
C12 C13 Br2 . . 119.6(2) ?
C13 C14 C15 . . 120.3(3) ?
C13 C14 H14A . . 119.9 ?
C15 C14 H14A . . 119.9 ?
C14 C15 C16 . . 120.0(3) ?
C14 C15 H15A . . 120.0 ?
C16 C15 H15A . . 120.0 ?
O2 C16 C17 . . 116.2(2) ?
O2 C16 C15 . . 124.6(2) ?
C17 C16 C15 . . 119.2(2) ?
C12 C17 C16 . . 120.6(2) ?
C12 C17 C9 . . 111.2(2) ?
C16 C17 C9 . . 128.2(2) ?
O1 C18 H18A . . 109.5 ?
O1 C18 H18B . . 109.5 ?
H18A C18 H18B . . 109.5 ?
O1 C18 H18C . . 109.5 ?
H18A C18 H18C . . 109.5 ?
H18B C18 H18C . . 109.5 ?
O2 C19 H19A . . 109.5 ?
O2 C19 H19B . . 109.5 ?
H19A C19 H19B . . 109.5 ?
O2 C19 H19C . . 109.5 ?
H19A C19 H19C . . 109.5 ?
H19B C19 H19C . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Br1 C1 . 1.907(3) ?
Br2 C13 . 1.903(3) ?
O1 C4 . 1.364(4) ?
O1 C18 . 1.417(4) ?
O2 C16 . 1.367(3) ?
O2 C19 . 1.408(4) ?
C1 C2 . 1.368(5) ?
C1 C6 . 1.389(4) ?
C2 C3 . 1.381(5) ?
C2 H2A . 0.9300 ?
C3 C4 . 1.386(4) ?
C3 H3A . 0.9300 ?
C4 C5 . 1.392(4) ?
C5 C6 . 1.390(4) ?
C5 C9 . 1.517(3) ?
C6 C7 . 1.493(4) ?
C7 C8 . 1.538(4) ?
C7 H7A . 0.9700 ?
C7 H7B . 0.9700 ?
C8 C9 . 1.554(4) ?
C8 H8A . 0.9700 ?
C8 H8B . 0.9700 ?
C9 C17 . 1.515(4) ?
C9 C10 . 1.551(4) ?
C10 C11 . 1.539(4) ?
C10 H10A . 0.9700 ?
C10 H10B . 0.9700 ?
C11 C12 . 1.502(4) ?
C11 H11A . 0.9700 ?
C11 H11B . 0.9700 ?
C12 C17 . 1.384(4) ?
C12 C13 . 1.386(4) ?
C13 C14 . 1.367(4) ?
C14 C15 . 1.387(4) ?
C14 H14A . 0.9300 ?
C15 C16 . 1.390(4) ?
C15 H15A . 0.9300 ?
C16 C17 . 1.386(4) ?
C18 H18A . 0.9600 ?
C18 H18B . 0.9600 ?
C18 H18C . 0.9600 ?
C19 H19A . 0.9600 ?
C19 H19B . 0.9600 ?
C19 H19C . 0.9600 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C18 H18A O1 2_667 2_667 0.96 2.56 3.416(6) 148.5 y
C19 H19A O2 2_656 2_656 0.96 2.52 3.365(2) 146.9 y
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 C1 C2 C3 . . . . -1.1(5) ?
Br1 C1 C2 C3 . . . . -178.9(2) ?
C1 C2 C3 C4 . . . . 0.4(5) ?
C18 O1 C4 C3 . . . . -3.1(5) ?
C18 O1 C4 C5 . . . . 176.9(4) ?
C2 C3 C4 O1 . . . . -179.0(3) ?
C2 C3 C4 C5 . . . . 1.0(4) ?
O1 C4 C5 C6 . . . . 178.4(3) ?
C3 C4 C5 C6 . . . . -1.5(4) ?
O1 C4 C5 C9 . . . . 0.8(4) ?
C3 C4 C5 C9 . . . . -179.2(3) ?
C2 C1 C6 C5 . . . . 0.5(5) ?
Br1 C1 C6 C5 . . . . 178.3(2) ?
C2 C1 C6 C7 . . . . -179.3(3) ?
Br1 C1 C6 C7 . . . . -1.5(5) ?
C4 C5 C6 C1 . . . . 0.8(4) ?
C9 C5 C6 C1 . . . . 178.8(2) ?
C4 C5 C6 C7 . . . . -179.4(3) ?
C9 C5 C6 C7 . . . . -1.4(3) ?
C1 C6 C7 C8 . . . . 165.1(3) ?
C5 C6 C7 C8 . . . . -14.7(4) ?
C6 C7 C8 C9 . . . . 24.5(3) ?
C6 C5 C9 C17 . . . . 138.9(3) ?
C4 C5 C9 C17 . . . . -43.4(4) ?
C6 C5 C9 C10 . . . . -103.8(3) ?
C4 C5 C9 C10 . . . . 74.0(4) ?
C6 C5 C9 C8 . . . . 16.5(3) ?
C4 C5 C9 C8 . . . . -165.7(3) ?
C7 C8 C9 C17 . . . . -151.6(3) ?
C7 C8 C9 C5 . . . . -24.9(3) ?
C7 C8 C9 C10 . . . . 94.8(3) ?
C17 C9 C10 C11 . . . . -26.4(3) ?
C5 C9 C10 C11 . . . . -153.3(3) ?
C8 C9 C10 C11 . . . . 93.2(3) ?
C9 C10 C11 C12 . . . . 25.7(3) ?
C10 C11 C12 C17 . . . . -15.2(3) ?
C10 C11 C12 C13 . . . . 164.8(3) ?
C17 C12 C13 C14 . . . . 0.0(4) ?
C11 C12 C13 C14 . . . . 180.0(3) ?
C17 C12 C13 Br2 . . . . 178.7(2) ?
C11 C12 C13 Br2 . . . . -1.3(4) ?
C12 C13 C14 C15 . . . . -0.5(4) ?
Br2 C13 C14 C15 . . . . -179.2(2) ?
C13 C14 C15 C16 . . . . 0.3(4) ?
C19 O2 C16 C17 . . . . 176.6(3) ?
C19 O2 C16 C15 . . . . -3.3(4) ?
C14 C15 C16 O2 . . . . -179.7(3) ?
C14 C15 C16 C17 . . . . 0.5(4) ?
C13 C12 C17 C16 . . . . 0.8(4) ?
C11 C12 C17 C16 . . . . -179.2(3) ?
C13 C12 C17 C9 . . . . 178.2(2) ?
C11 C12 C17 C9 . . . . -1.8(3) ?
O2 C16 C17 C12 . . . . 179.1(2) ?
C15 C16 C17 C12 . . . . -1.0(4) ?
O2 C16 C17 C9 . . . . 2.1(4) ?
C15 C16 C17 C9 . . . . -178.0(3) ?
C5 C9 C17 C12 . . . . 140.4(3) ?
C10 C9 C17 C12 . . . . 17.7(3) ?
C8 C9 C17 C12 . . . . -102.6(3) ?
C5 C9 C17 C16 . . . . -42.4(4) ?
C10 C9 C17 C16 . . . . -165.1(3) ?
C8 C9 C17 C16 . . . . 74.6(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9786626
