#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/59/2225935.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2225935
loop_
_publ_author_name
'Zhang, Cheng-Bo'
'Zhang, Hai-Quan'
'Li, Qing-Shan'
'Xing, Guang-Zhong'
_publ_section_title
;
 2',10'-Dibromospiro[cylohexane-1,6-dibenzo[d,f][1,3]dioxepine]
;
_journal_coeditor_code           NG2752
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1047
_journal_paper_doi               10.1107/S1600536810012535
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C18 H16 Br2 O2'
_chemical_formula_moiety         'C18 H16 Br2 O2'
_chemical_formula_sum            'C18 H16 Br2 O2'
_chemical_formula_weight         424.13
_chemical_name_systematic
;
2',10'-Dibromospiro[cylohexane-1,6-dibenzo[d,f][1,3]dioxepine]
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   17.793(4)
_cell_length_b                   10.143(5)
_cell_length_c                   18.279(5)
_cell_measurement_reflns_used    3788
_cell_measurement_temperature    290(2)
_cell_measurement_theta_max      54.84
_cell_measurement_theta_min      2.23
_cell_volume                     3299(2)
_computing_cell_refinement       'RAPID-AUTO (Rigaku, 1998)'
_computing_data_collection       'RAPID-AUTO (Rigaku, 1998)'
_computing_data_reduction        'CrystalStructure (Rigaku/MSC, 2002)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      290(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       'ω 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  0.0878
_diffrn_reflns_av_sigmaI/netI    0.0563
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            29533
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.05
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.919
_exptl_absorpt_correction_T_max  0.6137
_exptl_absorpt_correction_T_min  0.5673
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(ABSCOR; Higashi, 1995)'
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.708
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1680
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.354
_refine_diff_density_min         -0.638
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3735
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.999
_refine_ls_R_factor_all          0.0914
_refine_ls_R_factor_gt           0.0445
_refine_ls_shift/su_max          0.016
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0490P)²+1.6141P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0941
_refine_ls_wR_factor_ref         0.1111
_reflns_number_gt                2294
_reflns_number_total             3735
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            ng2752.cif
_cod_data_source_block           I
_cod_original_sg_symbol_Hall     '-P 2ac 2ab '
_cod_database_code               2225935
_cod_database_fobs_code          2225935
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, 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 1.04490(3) 0.06701(5) 0.35791(2) 0.07070(18) Uani d . 1 . .
Br Br2 0.85968(3) 0.22102(6) 0.73751(2) 0.0790(2) Uani d . 1 . .
C C1 1.0023(2) 0.2318(4) 0.38479(19) 0.0504(10) Uani d . 1 . .
C C2 1.0211(2) 0.3410(4) 0.3440(2) 0.0509(10) Uani d . 1 . .
H H2 1.0543 0.3341 0.3049 0.061 Uiso calc R 1 . .
C C3 0.9896(2) 0.4612(4) 0.36234(18) 0.0468(9) Uani d . 1 . .
H H3 1.0008 0.5357 0.3348 0.056 Uiso calc R 1 . .
C C4 0.94151(19) 0.4708(4) 0.42156(18) 0.0384(8) Uani d . 1 . .
C C5 0.92258(19) 0.3603(4) 0.46297(17) 0.0393(8) Uani d . 1 . .
C C6 0.9533(2) 0.2386(4) 0.44328(18) 0.0447(9) Uani d . 1 . .
H H6 0.9409 0.1629 0.4693 0.054 Uiso calc R 1 . .
C C7 0.8410(2) 0.3224(4) 0.65214(18) 0.0487(9) Uani d . 1 . .
C C8 0.8863(2) 0.3024(4) 0.59131(18) 0.0436(9) Uani d . 1 . .
H H8 0.9245 0.2400 0.5928 0.052 Uiso calc R 1 . .
C C9 0.87442(18) 0.3757(4) 0.52831(17) 0.0375(8) Uani d . 1 . .
C C10 0.81592(19) 0.4670(4) 0.52830(17) 0.0399(8) Uani d . 1 . .
C C11 0.7721(2) 0.4878(4) 0.5897(2) 0.0485(9) Uani d . 1 . .
H H11 0.7339 0.5504 0.5887 0.058 Uiso calc R 1 . .
C C12 0.7850(2) 0.4158(4) 0.65240(19) 0.0532(10) Uani d . 1 . .
H H12 0.7564 0.4302 0.6942 0.064 Uiso calc R 1 . .
C C13 0.84221(18) 0.6288(4) 0.43511(18) 0.0402(8) Uani d . 1 . .
C C14 0.8204(2) 0.6406(4) 0.35503(17) 0.0488(9) Uani d . 1 . .
H H14A 0.7663 0.6509 0.3512 0.059 Uiso calc R 1 . .
H H14B 0.8343 0.5603 0.3295 0.059 Uiso calc R 1 . .
C C15 0.8591(2) 0.7583(5) 0.3188(2) 0.0610(12) Uani d . 1 . .
H H15A 0.9128 0.7420 0.3163 0.073 Uiso calc R 1 . .
H H15B 0.8406 0.7681 0.2692 0.073 Uiso calc R 1 . .
C C16 0.8450(3) 0.8833(5) 0.3606(2) 0.0709(13) Uani d . 1 . .
H H16A 0.7919 0.9043 0.3588 0.085 Uiso calc R 1 . .
H H16B 0.8723 0.9551 0.3377 0.085 Uiso calc R 1 . .
C C17 0.8696(3) 0.8706(4) 0.4399(2) 0.0634(11) Uani d . 1 . .
H H17A 0.9236 0.8582 0.4420 0.076 Uiso calc R 1 . .
H H17B 0.8575 0.9511 0.4660 0.076 Uiso calc R 1 . .
C C18 0.8310(2) 0.7552(4) 0.4764(2) 0.0507(10) Uani d . 1 . .
H H18A 0.8506 0.7451 0.5256 0.061 Uiso calc R 1 . .
H H18B 0.7776 0.7735 0.4802 0.061 Uiso calc R 1 . .
O O1 0.91933(12) 0.5946(2) 0.44369(12) 0.0406(6) Uani d . 1 . .
O O2 0.79528(13) 0.5265(3) 0.46336(12) 0.0439(6) Uani d . 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
C2 C1 C6 . . 122.2(4) ?
C2 C1 Br1 . . 118.1(3) ?
C6 C1 Br1 . . 119.7(3) ?
C1 C2 C3 . . 118.7(3) ?
C1 C2 H2 . . 120.7 ?
C3 C2 H2 . . 120.7 ?
C4 C3 C2 . . 120.2(4) ?
C4 C3 H3 . . 119.9 ?
C2 C3 H3 . . 119.9 ?
O1 C4 C3 . . 118.2(3) ?
O1 C4 C5 . . 120.3(3) ?
C3 C4 C5 . . 121.2(3) ?
C4 C5 C6 . . 118.4(3) ?
C4 C5 C9 . . 119.6(3) ?
C6 C5 C9 . . 121.9(3) ?
C1 C6 C5 . . 119.4(4) ?
C1 C6 H6 . . 120.3 ?
C5 C6 H6 . . 120.3 ?
C12 C7 C8 . . 121.6(3) ?
C12 C7 Br2 . . 119.8(3) ?
C8 C7 Br2 . . 118.5(3) ?
C9 C8 C7 . . 119.9(3) ?
C9 C8 H8 . . 120.0 ?
C7 C8 H8 . . 120.0 ?
C8 C9 C10 . . 118.0(3) ?
C8 C9 C5 . . 121.8(3) ?
C10 C9 C5 . . 120.2(3) ?
O2 C10 C11 . . 118.7(3) ?
O2 C10 C9 . . 119.3(3) ?
C11 C10 C9 . . 121.5(3) ?
C12 C11 C10 . . 120.0(3) ?
C12 C11 H11 . . 120.0 ?
C10 C11 H11 . . 120.0 ?
C7 C12 C11 . . 118.9(3) ?
C7 C12 H12 . . 120.5 ?
C11 C12 H12 . . 120.5 ?
O1 C13 O2 . . 110.3(3) ?
O1 C13 C18 . . 106.3(3) ?
O2 C13 C18 . . 111.1(3) ?
O1 C13 C14 . . 111.8(3) ?
O2 C13 C14 . . 104.8(3) ?
C18 C13 C14 . . 112.6(3) ?
C13 C14 C15 . . 111.3(3) ?
C13 C14 H14A . . 109.4 ?
C15 C14 H14A . . 109.4 ?
C13 C14 H14B . . 109.4 ?
C15 C14 H14B . . 109.4 ?
H14A C14 H14B . . 108.0 ?
C16 C15 C14 . . 111.3(3) ?
C16 C15 H15A . . 109.4 ?
C14 C15 H15A . . 109.4 ?
C16 C15 H15B . . 109.4 ?
C14 C15 H15B . . 109.4 ?
H15A C15 H15B . . 108.0 ?
C15 C16 C17 . . 111.4(4) ?
C15 C16 H16A . . 109.3 ?
C17 C16 H16A . . 109.3 ?
C15 C16 H16B . . 109.3 ?
C17 C16 H16B . . 109.3 ?
H16A C16 H16B . . 108.0 ?
C18 C17 C16 . . 110.8(4) ?
C18 C17 H17A . . 109.5 ?
C16 C17 H17A . . 109.5 ?
C18 C17 H17B . . 109.5 ?
C16 C17 H17B . . 109.5 ?
H17A C17 H17B . . 108.1 ?
C13 C18 C17 . . 112.2(3) ?
C13 C18 H18A . . 109.2 ?
C17 C18 H18A . . 109.2 ?
C13 C18 H18B . . 109.2 ?
C17 C18 H18B . . 109.2 ?
H18A C18 H18B . . 107.9 ?
C4 O1 C13 . . 117.8(3) ?
C10 O2 C13 . . 118.2(3) ?
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 . 1.900(4) ?
Br2 C7 . 1.898(4) ?
C1 C2 . 1.377(6) ?
C1 C6 . 1.381(5) ?
C2 C3 . 1.382(6) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.384(5) ?
C3 H3 . 0.9300 ?
C4 O1 . 1.376(4) ?
C4 C5 . 1.394(5) ?
C5 C6 . 1.398(5) ?
C5 C9 . 1.478(5) ?
C6 H6 . 0.9300 ?
C7 C12 . 1.374(5) ?
C7 C8 . 1.388(5) ?
C8 C9 . 1.387(5) ?
C8 H8 . 0.9300 ?
C9 C10 . 1.394(5) ?
C10 O2 . 1.381(4) ?
C10 C11 . 1.383(5) ?
C11 C12 . 1.379(5) ?
C11 H11 . 0.9300 ?
C12 H12 . 0.9300 ?
C13 O1 . 1.424(4) ?
C13 O2 . 1.428(4) ?
C13 C18 . 1.501(5) ?
C13 C14 . 1.519(5) ?
C14 C15 . 1.530(5) ?
C14 H14A . 0.9700 ?
C14 H14B . 0.9700 ?
C15 C16 . 1.502(6) ?
C15 H15A . 0.9700 ?
C15 H15B . 0.9700 ?
C16 C17 . 1.521(6) ?
C16 H16A . 0.9700 ?
C16 H16B . 0.9700 ?
C17 C18 . 1.512(6) ?
C17 H17A . 0.9700 ?
C17 H17B . 0.9700 ?
C18 H18A . 0.9700 ?
C18 H18B . 0.9700 ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24744829
