#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/69/2016932.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_2016932
loop_
_publ_author_name
'Burns, Dennis H.'
'Meece, F. Alex'
'Moore, Curtis E.'
'Eichhorn, David M.'
_publ_section_title
;
 Two similar dibenzo cyclic ethers with dissimilar conformations
;
_journal_coeditor_code           SK3262
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o27
_journal_page_last               o30
_journal_paper_doi               10.1107/S0108270108040882
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C16 H14 Br2 O2'
_chemical_formula_moiety         'C16 H14 Br2 O2'
_chemical_formula_sum            'C16 H14 Br2 O2'
_chemical_formula_weight         398.09
_chemical_name_common
;
6,12-dibromodibenzo[d,i]-1,2,3,6,7,8-hexahydro-1,3-dioxecin
;
_chemical_name_systematic
;
8,16-dibromo-2,4-dioxatricyclo[12.4.0.0^5,10^]octadeca-5,7,9,14,16,18-hexaene
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'SHELXL97 (Sheldrick, 2008)'
_cell_angle_alpha                90.00
_cell_angle_beta                 97.9690(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   21.3204(5)
_cell_length_b                   8.8456(2)
_cell_length_c                   7.8155(2)
_cell_measurement_reflns_used    5967
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      26
_cell_measurement_theta_min      3.5
_cell_volume                     1459.71(6)
_computing_cell_refinement       'APEX2 (Bruker, 2005)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'SAINT (Bruker, 1996)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area-detector'
_diffrn_measurement_method       'φ and 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  0.0530
_diffrn_reflns_av_sigmaI/netI    0.0272
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            26317
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         3.50
_exptl_absorpt_coefficient_mu    5.551
_exptl_absorpt_correction_T_max  0.4999
_exptl_absorpt_correction_T_min  0.3398
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Sheldrick, 2002)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.811
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.380
_refine_diff_density_min         -0.463
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2860
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.0364
_refine_ls_R_factor_gt           0.0262
_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)+(0.0157P)²+1.7696P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0528
_refine_ls_wR_factor_ref         0.0563
_reflns_number_gt                2415
_reflns_number_total             2860
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sk3262.cif
_cod_data_source_block           II
_cod_original_cell_volume        1459.70(6)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2016932
_cod_database_fobs_code          2016932
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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 Br2 0.495545(13) 0.31359(3) 0.26183(4) 0.02697(9) Uani d . 1 . .
Br Br1 0.941196(15) 0.49131(4) -0.37098(4) 0.03785(10) Uani d . 1 . .
C C1 0.89960(13) 0.4979(3) -0.1706(4) 0.0254(6) Uani d . 1 . .
C C2 0.92491(13) 0.5843(3) -0.0303(4) 0.0250(6) Uani d . 1 . .
H H2 0.9613 0.6415 -0.0337 0.030 Uiso calc R 1 . .
C C3 0.89466(13) 0.5832(3) 0.1151(4) 0.0244(6) Uani d . 1 . .
H H3 0.9111 0.6393 0.2116 0.029 Uiso calc R 1 . .
C C4 0.84000(13) 0.4991(3) 0.1177(3) 0.0197(6) Uani d . 1 . .
C C5 0.81399(13) 0.4130(3) -0.0242(3) 0.0197(6) Uani d . 1 . .
C C6 0.84548(13) 0.4144(3) -0.1689(4) 0.0245(6) Uani d . 1 . .
H H6 0.8296 0.3580 -0.2656 0.029 Uiso calc R 1 . .
C C7 0.75441(13) 0.3210(3) -0.0267(3) 0.0205(6) Uani d . 1 . .
H H7A 0.7439 0.3147 0.0900 0.025 Uiso calc R 1 . .
H H7B 0.7624 0.2191 -0.0641 0.025 Uiso calc R 1 . .
C C8 0.69766(12) 0.3856(3) -0.1449(3) 0.0200(6) Uani d . 1 . .
H H8A 0.6633 0.3130 -0.1542 0.024 Uiso calc R 1 . .
H H8B 0.7093 0.3999 -0.2594 0.024 Uiso calc R 1 . .
C C9 0.67412(13) 0.5368(3) -0.0809(3) 0.0203(6) Uani d . 1 . .
H H9A 0.7087 0.6090 -0.0693 0.024 Uiso calc R 1 . .
H H9B 0.6408 0.5758 -0.1666 0.024 Uiso calc R 1 . .
C C10 0.64926(13) 0.5234(3) 0.0897(3) 0.0190(6) Uani d . 1 . .
C C11 0.59357(13) 0.4441(3) 0.0996(3) 0.0197(6) Uani d . 1 . .
H H11 0.5712 0.4026 0.0000 0.024 Uiso calc R 1 . .
C C12 0.57120(12) 0.4265(3) 0.2551(4) 0.0199(6) Uani d . 1 . .
C C13 0.60248(13) 0.4884(3) 0.4063(3) 0.0215(6) Uani d . 1 . .
H H13 0.5869 0.4753 0.5107 0.026 Uiso calc R 1 . .
C C14 0.65715(13) 0.5698(3) 0.3983(3) 0.0207(6) Uani d . 1 . .
H H14 0.6785 0.6137 0.4979 0.025 Uiso calc R 1 . .
C C15 0.68039(13) 0.5865(3) 0.2412(3) 0.0187(6) Uani d . 1 . .
C C16 0.79036(13) 0.6263(3) 0.3318(3) 0.0243(6) Uani d . 1 . .
H H16A 0.8226 0.7035 0.3310 0.029 Uiso calc R 1 . .
H H16B 0.7827 0.6124 0.4502 0.029 Uiso calc R 1 . .
O O1 0.81220(9) 0.4898(2) 0.2689(2) 0.0223(4) Uani d . 1 . .
O O2 0.73395(8) 0.6748(2) 0.2300(2) 0.0217(4) 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
C6 C1 C2 . . 121.7(3) ?
C6 C1 Br1 . . 118.7(2) ?
C2 C1 Br1 . . 119.6(2) ?
C3 C2 C1 . . 118.2(3) ?
C3 C2 H2 . . 120.9 ?
C1 C2 H2 . . 120.9 ?
C2 C3 C4 . . 120.3(3) ?
C2 C3 H3 . . 119.8 ?
C4 C3 H3 . . 119.8 ?
C3 C4 C5 . . 121.6(3) ?
C3 C4 O1 . . 120.1(2) ?
C5 C4 O1 . . 118.2(2) ?
C6 C5 C4 . . 117.2(3) ?
C6 C5 C7 . . 119.6(2) ?
C4 C5 C7 . . 123.2(2) ?
C1 C6 C5 . . 120.9(3) ?
C1 C6 H6 . . 119.5 ?
C5 C6 H6 . . 119.5 ?
C5 C7 C8 . . 113.6(2) ?
C5 C7 H7A . . 108.8 ?
C8 C7 H7A . . 108.8 ?
C5 C7 H7B . . 108.8 ?
C8 C7 H7B . . 108.8 ?
H7A C7 H7B . . 107.7 ?
C7 C8 C9 . . 113.3(2) ?
C7 C8 H8A . . 108.9 ?
C9 C8 H8A . . 108.9 ?
C7 C8 H8B . . 108.9 ?
C9 C8 H8B . . 108.9 ?
H8A C8 H8B . . 107.7 ?
C10 C9 C8 . . 113.0(2) ?
C10 C9 H9A . . 109.0 ?
C8 C9 H9A . . 109.0 ?
C10 C9 H9B . . 109.0 ?
C8 C9 H9B . . 109.0 ?
H9A C9 H9B . . 107.8 ?
C11 C10 C15 . . 117.7(2) ?
C11 C10 C9 . . 119.8(2) ?
C15 C10 C9 . . 122.5(2) ?
C12 C11 C10 . . 120.7(3) ?
C12 C11 H11 . . 119.7 ?
C10 C11 H11 . . 119.7 ?
C11 C12 C13 . . 121.6(3) ?
C11 C12 Br2 . . 118.9(2) ?
C13 C12 Br2 . . 119.5(2) ?
C14 C13 C12 . . 118.5(2) ?
C14 C13 H13 . . 120.7 ?
C12 C13 H13 . . 120.7 ?
C13 C14 C15 . . 120.0(2) ?
C13 C14 H14 . . 120.0 ?
C15 C14 H14 . . 120.0 ?
C10 C15 C14 . . 121.4(2) ?
C10 C15 O2 . . 117.9(2) ?
C14 C15 O2 . . 120.5(2) ?
O1 C16 O2 . . 111.1(2) ?
O1 C16 H16A . . 109.4 ?
O2 C16 H16A . . 109.4 ?
O1 C16 H16B . . 109.4 ?
O2 C16 H16B . . 109.4 ?
H16A C16 H16B . . 108.0 ?
C4 O1 C16 . . 116.4(2) y
C15 O2 C16 . . 115.8(2) y
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
Br2 C12 . 1.904(3) n
Br1 C1 . 1.904(3) n
C1 C6 . 1.372(4) n
C1 C2 . 1.383(4) n
C2 C3 . 1.382(4) n
C2 H2 . 0.9300 ?
C3 C4 . 1.385(4) n
C3 H3 . 0.9300 ?
C4 C5 . 1.395(4) y
C4 O1 . 1.397(3) y
C5 C6 . 1.393(4) n
C5 C7 . 1.507(4) y
C6 H6 . 0.9300 ?
C7 C8 . 1.528(4) y
C7 H7A . 0.9700 ?
C7 H7B . 0.9700 ?
C8 C9 . 1.536(4) y
C8 H8A . 0.9700 ?
C8 H8B . 0.9700 ?
C9 C10 . 1.506(4) y
C9 H9A . 0.9700 ?
C9 H9B . 0.9700 ?
C10 C11 . 1.390(4) n
C10 C15 . 1.392(4) y
C11 C12 . 1.375(4) n
C11 H11 . 0.9300 ?
C12 C13 . 1.386(4) n
C13 C14 . 1.379(4) n
C13 H13 . 0.9300 ?
C14 C15 . 1.394(4) n
C14 H14 . 0.9300 ?
C15 O2 . 1.396(3) y
C16 O1 . 1.407(3) y
C16 O2 . 1.413(3) y
C16 H16A . 0.9700 ?
C16 H16B . 0.9700 ?
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
C16 O1 C4 C3 . . . . 62.4(3) no
C16 O1 C4 C5 . . . . -122.3(3) no
C4 O1 C16 O2 . . . . 74.2(3) no
C16 O2 C15 C10 . . . . -122.0(2) no
C16 O2 C15 C14 . . . . 61.5(3) no
C15 O2 C16 O1 . . . . 69.0(3) no
Br1 C1 C6 C5 . . . . 178.7(2) no
Br1 C1 C2 C3 . . . . -178.1(2) no
C6 C1 C2 C3 . . . . 0.9(4) no
C2 C1 C6 C5 . . . . -0.4(4) no
C1 C2 C3 C4 . . . . -0.9(4) no
C2 C3 C4 O1 . . . . 175.4(2) no
C2 C3 C4 C5 . . . . 0.3(4) no
O1 C4 C5 C7 . . . . 5.2(4) no
C3 C4 C5 C6 . . . . 0.3(4) no
O1 C4 C5 C6 . . . . -174.9(2) no
C3 C4 C5 C7 . . . . -179.6(3) no
C4 C5 C6 C1 . . . . -0.3(4) no
C7 C5 C6 C1 . . . . 179.6(3) no
C6 C5 C7 C8 . . . . -70.8(3) no
C4 C5 C7 C8 . . . . 109.1(3) no
C5 C7 C8 C9 . . . . -67.6(3) no
C7 C8 C9 C10 . . . . -63.8(3) no
C8 C9 C10 C11 . . . . -68.3(3) no
C8 C9 C10 C15 . . . . 111.0(3) no
C9 C10 C15 O2 . . . . 5.0(4) no
C11 C10 C15 C14 . . . . 0.7(4) no
C9 C10 C15 C14 . . . . -178.6(2) no
C11 C10 C15 O2 . . . . -175.8(2) no
C9 C10 C11 C12 . . . . 177.9(2) no
C15 C10 C11 C12 . . . . -1.4(4) no
C10 C11 C12 Br2 . . . . -178.8(2) no
C10 C11 C12 C13 . . . . 1.0(4) no
Br2 C12 C13 C14 . . . . -180.0(2) no
C11 C12 C13 C14 . . . . 0.3(4) no
C12 C13 C14 C15 . . . . -1.0(4) no
C13 C14 C15 O2 . . . . 176.9(2) no
C13 C14 C15 C10 . . . . 0.5(4) no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24726350
