#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:44:30 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178441 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/62/4026255.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_4026255
loop_
_publ_author_name
'Faiz Ahmed Khan'
'Ch. Nageswara Rao'
_publ_section_title
;
 Grob Fragmentation of Norbornyl α-Diketones: A Route to α-Ketoenols and
 Aromatic Compounds
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3320
_journal_page_last               3328
_journal_paper_doi               10.1021/jo200223a
_journal_volume                  76
_journal_year                    2011
_chemical_formula_moiety         'C12 H14 Br2 O6'
_chemical_formula_sum            'C12 H14 Br2 O6'
_chemical_formula_weight         414.05
_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           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 95.193(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.928(2)
_cell_length_b                   8.502(3)
_cell_length_c                   25.635(8)
_cell_measurement_reflns_used    2576
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.42
_cell_measurement_theta_min      2.53
_cell_volume                     1503.8(8)
_computing_cell_refinement       'SAINT 6.45  (Bruker, 2003)'
_computing_data_collection       'SMART 5.628 (Bruker, 2003)'
_computing_data_reduction        'SAINT 6.45  (Bruker, 2003)'
_computing_molecular_graphics    'Diamond 2.1'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    SIR-92
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'CCD area Detector'
_diffrn_measurement_method       'phi and omega 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  0.0439
_diffrn_reflns_av_sigmaI/netI    0.0601
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            9573
_diffrn_reflns_theta_full        28.44
_diffrn_reflns_theta_max         28.44
_diffrn_reflns_theta_min         2.52
_diffrn_standards_decay_%        0.5
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    5.411
_exptl_absorpt_correction_T_max  0.5397
_exptl_absorpt_correction_T_min  0.4425
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS 2.10 (Bruker 2003)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.829
_exptl_crystal_description       prism
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.820
_refine_diff_density_min         -0.476
_refine_diff_density_rms         0.109
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         3704
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0816
_refine_ls_R_factor_gt           0.0436
_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)+(0.0376P)²+2.5789P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0935
_refine_ls_wR_factor_ref         0.1291
_reflns_number_gt                2376
_reflns_number_total             3704
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo200223a_si_002.cif
_cod_data_source_block           11decdm
_cod_original_cell_volume        1503.6(8)
_cod_database_code               4026255
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_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
C1 C 0.8364(7) 0.3181(5) 0.13604(17) 0.0384(10) Uani 1 1 d .
C2 C 0.7811(7) 0.3210(5) 0.19053(16) 0.0366(10) Uani 1 1 d .
C3 C 0.6068(7) 0.2750(5) 0.20074(16) 0.0392(10) Uani 1 1 d .
C4 C 0.4465(7) 0.2220(6) 0.16203(18) 0.0473(11) Uani 1 1 d .
H4A H 0.3524 0.3062 0.1565 0.057 Uiso 1 1 calc R
H4B H 0.3820 0.1328 0.1764 0.057 Uiso 1 1 calc R
C5 C 0.5165(7) 0.1747(5) 0.10878(18) 0.0414(10) Uani 1 1 d .
C6 C 0.6693(7) 0.2903(5) 0.09288(18) 0.0401(10) Uani 1 1 d .
C7 C 0.6035(8) 0.0085(5) 0.1156(2) 0.0483(11) Uani 1 1 d .
C8 C 0.8830(9) -0.1360(6) 0.1420(2) 0.0665(16) Uani 1 1 d .
H8A H 1.0109 -0.1201 0.1589 0.100 Uiso 1 1 calc R
H8B H 0.8920 -0.1788 0.1077 0.100 Uiso 1 1 calc R
H8C H 0.8134 -0.2079 0.1623 0.100 Uiso 1 1 calc R
C9 C 0.7544(7) 0.2394(6) 0.04277(19) 0.0448(11) Uani 1 1 d .
C10 C 0.9057(10) 0.3061(8) -0.0312(2) 0.0762(18) Uani 1 1 d .
H10A H 0.9463 0.3971 -0.0495 0.114 Uiso 1 1 calc R
H10B H 0.8139 0.2473 -0.0537 0.114 Uiso 1 1 calc R
H10C H 1.0162 0.2412 -0.0210 0.114 Uiso 1 1 calc R
C11 C 0.9920(9) 0.5147(6) 0.2292(2) 0.0648(16) Uani 1 1 d .
H11A H 1.0926 0.5276 0.2572 0.097 Uiso 1 1 calc R
H11B H 0.8866 0.5845 0.2345 0.097 Uiso 1 1 calc R
H11C H 1.0422 0.5385 0.1964 0.097 Uiso 1 1 calc R
C12 C 0.3389(7) 0.1660(7) 0.0678(2) 0.0566(14) Uani 1 1 d .
H12A H 0.2821 0.2686 0.0631 0.085 Uiso 1 1 calc R
H12B H 0.2451 0.0945 0.0798 0.085 Uiso 1 1 calc R
H12C H 0.3792 0.1294 0.0350 0.085 Uiso 1 1 calc R
O1 O 0.9988(5) 0.3422(5) 0.12581(14) 0.0605(10) Uani 1 1 d .
O2 O 0.9245(5) 0.3566(4) 0.22848(12) 0.0469(8) Uani 1 1 d .
O3 O 0.7639(6) 0.1034(5) 0.03180(14) 0.0688(11) Uani 1 1 d .
O4 O 0.8170(6) 0.3547(4) 0.01466(14) 0.0629(10) Uani 1 1 d .
O5 O 0.7835(5) 0.0099(4) 0.13781(13) 0.0496(8) Uani 1 1 d .
O6 O 0.5142(6) -0.1091(4) 0.10502(17) 0.0741(12) Uani 1 1 d .
Br1 Br 0.56061(8) 0.50521(6) 0.08498(2) 0.05700(19) Uani 1 1 d .
Br2 Br 0.54426(9) 0.27872(7) 0.27152(2) 0.0646(2) Uani 1 1 d .
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
O1 C1 C2 122.2(4)
O1 C1 C6 121.9(4)
C2 C1 C6 115.9(4)
C3 C2 O2 123.2(4)
C3 C2 C1 120.1(4)
O2 C2 C1 116.3(4)
C2 C3 C4 126.7(4)
C2 C3 Br2 118.4(3)
C4 C3 Br2 114.8(3)
C3 C4 C5 113.2(4)
C6 C5 C7 110.3(4)
C6 C5 C4 110.5(4)
C7 C5 C4 106.9(4)
C6 C5 C12 112.2(4)
C7 C5 C12 108.2(4)
C4 C5 C12 108.6(4)
C9 C6 C5 111.9(4)
C9 C6 C1 109.0(4)
C5 C6 C1 113.6(4)
C9 C6 Br1 110.4(3)
C5 C6 Br1 110.8(3)
C1 C6 Br1 100.7(3)
O6 C7 O5 123.6(5)
O6 C7 C5 123.6(5)
O5 C7 C5 112.6(4)
O3 C9 O4 124.5(5)
O3 C9 C6 120.5(5)
O4 C9 C6 115.0(4)
C2 O2 C11 115.9(3)
C9 O4 C10 114.9(4)
C7 O5 C8 117.2(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O1 1.196(5)
C1 C2 1.482(6)
C1 C6 1.545(6)
C2 C3 1.317(6)
C2 O2 1.360(5)
C3 C4 1.490(6)
C3 Br2 1.904(4)
C4 C5 1.542(6)
C5 C6 1.526(7)
C5 C7 1.540(6)
C5 C12 1.546(6)
C6 C9 1.524(6)
C6 Br1 1.980(4)
C7 O6 1.194(6)
C7 O5 1.323(6)
C8 O5 1.418(6)
C9 O3 1.194(6)
C9 O4 1.313(6)
C10 O4 1.436(6)
C11 O2 1.423(6)
