#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:44:30 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178441 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/62/4026256.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_4026256
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         'C15 H14 Br2 O4'
_chemical_formula_sum            'C15 H14 Br2 O4'
_chemical_formula_weight         418.08
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 107.725(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.838(3)
_cell_length_b                   13.901(3)
_cell_length_c                   12.084(3)
_cell_measurement_reflns_used    2208
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.94
_cell_measurement_theta_min      2.30
_cell_volume                     1574.1(7)
_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      293(2)
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_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  0.0449
_diffrn_reflns_av_sigmaI/netI    0.0590
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            10257
_diffrn_reflns_theta_full        28.41
_diffrn_reflns_theta_max         28.41
_diffrn_reflns_theta_min         2.30
_diffrn_standards_decay_%        0.5
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    5.161
_exptl_absorpt_correction_T_max  0.5535
_exptl_absorpt_correction_T_min  0.4568
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS 2.10 (Bruker 2003)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.764
_exptl_crystal_description       prism
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.700
_refine_diff_density_min         -1.148
_refine_diff_density_rms         0.210
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         3899
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0940
_refine_ls_R_factor_gt           0.0494
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0740P)²+3.9621P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1161
_refine_ls_wR_factor_ref         0.1721
_reflns_number_gt                2420
_reflns_number_total             3899
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo200223a_si_003.cif
_cod_data_source_block           28marh
_cod_original_cell_volume        1574.2(7)
_cod_database_code               4026256
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
Br1 Br 0.47069(8) 0.05478(5) 0.86731(6) 0.0525(2) Uani 1 1 d .
Br2 Br 0.81112(7) 0.30202(5) 0.57327(6) 0.0552(2) Uani 1 1 d .
O1 O 0.6534(4) 0.1195(3) 0.5149(3) 0.0413(9) Uani 1 1 d .
H1 H 0.6079 0.0693 0.4989 0.062 Uiso 1 1 calc R
O4 O 0.3533(5) 0.2670(3) 0.8050(4) 0.0491(10) Uani 1 1 d .
O3 O 0.3020(5) 0.2097(4) 0.6240(4) 0.0605(13) Uani 1 1 d .
O2 O 0.4860(5) 0.0322(3) 0.6225(4) 0.0507(11) Uani 1 1 d .
C7 C 0.3769(6) 0.2139(4) 0.7233(5) 0.0376(12) Uani 1 1 d .
C10 C 0.6116(6) 0.3771(4) 0.7511(5) 0.0405(13) Uani 1 1 d .
C6 C 0.6381(5) 0.1566(4) 0.6136(5) 0.0338(11) Uani 1 1 d .
C3 C 0.6446(6) 0.2097(4) 0.8401(5) 0.0379(12) Uani 1 1 d .
H3A H 0.7202 0.1640 0.8746 0.045 Uiso 1 1 calc R
H3B H 0.6215 0.2424 0.9030 0.045 Uiso 1 1 calc R
C4 C 0.5141(6) 0.1546(4) 0.7693(4) 0.0311(11) Uani 1 1 d .
C2 C 0.7010(6) 0.2843(4) 0.7710(5) 0.0381(12) Uani 1 1 d .
C5 C 0.5433(6) 0.1073(4) 0.6654(4) 0.0338(11) Uani 1 1 d .
C9 C 0.8560(6) 0.3063(5) 0.8467(6) 0.0499(15) Uani 1 1 d .
H9A H 0.8547 0.3350 0.9186 0.075 Uiso 1 1 calc R
H9B H 0.8995 0.3499 0.8059 0.075 Uiso 1 1 calc R
H9C H 0.9098 0.2475 0.8624 0.075 Uiso 1 1 calc R
C1 C 0.7029(6) 0.2392(4) 0.6584(5) 0.0372(12) Uani 1 1 d .
C15 C 0.5205(7) 0.4027(5) 0.6431(6) 0.0508(15) Uani 1 1 d .
H15 H 0.5135 0.3629 0.5797 0.061 Uiso 1 1 calc R
C11 C 0.6190(8) 0.4378(5) 0.8441(7) 0.0631(19) Uani 1 1 d .
H11 H 0.6794 0.4221 0.9174 0.076 Uiso 1 1 calc R
C8 C 0.2300(8) 0.3289(6) 0.7714(7) 0.069(2) Uani 1 1 d .
H8A H 0.2235 0.3641 0.8379 0.104 Uiso 1 1 calc R
H8B H 0.1456 0.2907 0.7408 0.104 Uiso 1 1 calc R
H8C H 0.2389 0.3732 0.7130 0.104 Uiso 1 1 calc R
C14 C 0.4396(9) 0.4863(5) 0.6271(8) 0.071(2) Uani 1 1 d .
H14 H 0.3798 0.5023 0.5537 0.085 Uiso 1 1 calc R
C13 C 0.4483(10) 0.5449(6) 0.7198(11) 0.084(3) Uani 1 1 d .
H13 H 0.3941 0.6008 0.7097 0.101 Uiso 1 1 calc R
C12 C 0.5390(10) 0.5204(6) 0.8301(9) 0.081(3) Uani 1 1 d .
H12 H 0.5450 0.5599 0.8936 0.097 Uiso 1 1 calc R
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
C7 O4 C8 116.9(5)
O3 C7 O4 125.7(6)
O3 C7 C4 122.7(5)
O4 C7 C4 111.6(5)
C15 C10 C11 117.8(6)
C15 C10 C2 122.5(5)
C11 C10 C2 119.7(6)
C1 C6 O1 121.0(5)
C1 C6 C5 121.4(5)
O1 C6 C5 117.6(5)
C4 C3 C2 114.7(4)
C3 C4 C5 110.1(4)
C3 C4 C7 115.7(4)
C5 C4 C7 107.4(4)
C3 C4 Br1 108.7(3)
C5 C4 Br1 108.9(3)
C7 C4 Br1 105.7(3)
C1 C2 C10 111.9(5)
C1 C2 C3 108.4(4)
C10 C2 C3 111.5(5)
C1 C2 C9 109.6(5)
C10 C2 C9 109.9(5)
C3 C2 C9 105.4(5)
O2 C5 C6 119.7(5)
O2 C5 C4 122.7(5)
C6 C5 C4 117.5(5)
C6 C1 C2 125.8(5)
C6 C1 Br2 116.7(4)
C2 C1 Br2 117.4(4)
C10 C15 C14 121.6(7)
C12 C11 C10 121.4(8)
C13 C14 C15 119.7(8)
C14 C13 C12 119.9(8)
C11 C12 C13 119.6(8)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C4 1.954(5)
Br2 C1 1.903(5)
O1 C6 1.349(6)
O4 C7 1.309(7)
O4 C8 1.441(8)
O3 C7 1.204(7)
O2 C5 1.223(6)
C7 C4 1.533(8)
C10 C15 1.386(9)
C10 C11 1.389(9)
C10 C2 1.538(8)
C6 C1 1.345(8)
C6 C5 1.445(8)
C3 C4 1.516(7)
C3 C2 1.538(8)
C4 C5 1.521(7)
C2 C1 1.504(8)
C2 C9 1.551(8)
C15 C14 1.388(10)
C11 C12 1.374(11)
C14 C13 1.365(13)
C13 C12 1.402(14)
