#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/62/4026257.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_4026257
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         'C10 H9 B1 Br2 F2 O6'
_chemical_formula_sum            'C10 H9 B Br2 F2 O6'
_chemical_formula_weight         433.77
_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                90.000(5)
_cell_angle_beta                 99.987(5)
_cell_angle_gamma                90.000(5)
_cell_formula_units_Z            4
_cell_length_a                   6.778(5)
_cell_length_b                   10.779(5)
_cell_length_c                   18.776(5)
_cell_measurement_temperature    100(2)
_cell_volume                     1351.0(12)
_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 0.990
_diffrn_measured_fraction_theta_max 0.990
_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     0.71069
_diffrn_reflns_av_R_equivalents  0.0673
_diffrn_reflns_av_sigmaI/netI    0.0590
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8758
_diffrn_reflns_theta_full        28.28
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         2.19
_diffrn_standards_decay_%        0.5
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    6.013
_exptl_absorpt_correction_T_max  1.1009
_exptl_absorpt_correction_T_min  0.9876
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS 2.10 (Bruker 2003)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    2.036
_exptl_crystal_description       prism
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.13
_refine_diff_density_max         1.255
_refine_diff_density_min         -0.611
_refine_diff_density_rms         0.134
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         3309
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.0400
_refine_ls_R_factor_gt           0.0337
_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)+(0.0475P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0851
_refine_ls_wR_factor_ref         0.0879
_reflns_number_gt                2876
_reflns_number_total             3309
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo200223a_si_004.cif
_cod_data_source_block           17marem
_cod_original_formula_sum        'C10 H9 B1 Br2 F2 O6'
_cod_database_code               4026257
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
Br1 Br 0.36649(4) 0.08377(3) 0.069348(14) 0.01787(10) Uani 1 1 d .
Br2 Br 0.34075(4) -0.13730(2) 0.178250(14) 0.01651(10) Uani 1 1 d .
O1 O -0.0005(3) 0.25056(19) 0.14283(10) 0.0197(4) Uani 1 1 d .
O2 O -0.1732(3) 0.16407(18) 0.04181(10) 0.0159(4) Uani 1 1 d .
O3 O 0.2698(3) 0.14284(18) 0.33648(10) 0.0157(4) Uani 1 1 d .
F2 F 0.1271(3) 0.25212(16) 0.42178(9) 0.0226(4) Uani 1 1 d .
F1 F 0.2983(3) 0.07474(16) 0.45499(9) 0.0212(4) Uani 1 1 d .
O6 O -0.2609(3) -0.03772(18) 0.31160(10) 0.0142(4) Uani 1 1 d .
O7 O 0.4683(3) 0.16278(18) 0.22592(10) 0.0168(4) Uani 1 1 d .
C1 C -0.0517(4) 0.1612(3) 0.10540(14) 0.0132(5) Uani 1 1 d .
C2 C 0.0132(4) 0.0287(2) 0.12635(13) 0.0127(5) Uani 1 1 d .
H2 H -0.0250 -0.0260 0.0845 0.015 Uiso 1 1 calc R
C3 C -0.0899(4) -0.0157(3) 0.18908(13) 0.0133(5) Uani 1 1 d .
H3A H -0.2302 0.0077 0.1789 0.016 Uiso 1 1 calc R
H3B H -0.0832 -0.1055 0.1919 0.016 Uiso 1 1 calc R
C4 C -0.0924(4) 0.0217(3) 0.32245(14) 0.0133(5) Uani 1 1 d .
O8 O -0.0209(3) 0.06205(18) 0.38511(10) 0.0158(4) Uani 1 1 d .
B B 0.1750(5) 0.1359(3) 0.40117(16) 0.0145(6) Uani 1 1 d .
C7 C 0.3139(4) 0.1057(2) 0.21623(14) 0.0120(5) Uani 1 1 d .
C22 C 0.2406(4) 0.0285(2) 0.14855(13) 0.0124(5) Uani 1 1 d .
C9 C 0.0043(4) 0.0377(2) 0.26053(13) 0.0122(5) Uani 1 1 d .
C10 C 0.1859(4) 0.0948(2) 0.27399(13) 0.0122(5) Uani 1 1 d .
C11 C -0.2485(5) 0.2869(3) 0.01847(15) 0.0214(6) Uani 1 1 d .
H11A H -0.3344 0.2806 -0.0278 0.032 Uiso 1 1 calc R
H11B H -0.1379 0.3406 0.0146 0.032 Uiso 1 1 calc R
H11C H -0.3228 0.3202 0.0532 0.032 Uiso 1 1 calc R
C12 C -0.3571(5) -0.0629(3) 0.37383(15) 0.0196(6) Uani 1 1 d .
H12A H -0.4799 -0.1072 0.3583 0.029 Uiso 1 1 calc R
H12B H -0.3853 0.0140 0.3958 0.029 Uiso 1 1 calc R
H12C H -0.2694 -0.1121 0.4084 0.029 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'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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
C1 O2 C11 114.9(2)
C10 O3 B 122.1(2)
C4 O6 C12 118.1(2)
O1 C1 O2 125.2(3)
O1 C1 C2 123.7(2)
O2 C1 C2 111.1(2)
C22 C2 C1 107.7(2)
C22 C2 C3 111.1(2)
C1 C2 C3 109.7(2)
C9 C3 C2 112.6(2)
O8 C4 O6 120.0(2)
O8 C4 C9 123.6(3)
O6 C4 C9 116.4(2)
C4 O8 B 122.6(2)
F1 B F2 112.2(2)
F1 B O3 109.7(2)
F2 B O3 110.2(2)
F1 B O8 107.1(2)
F2 B O8 106.9(2)
O3 B O8 110.6(2)
O7 C7 C10 121.8(2)
O7 C7 C22 123.7(2)
C10 C7 C22 114.3(2)
C2 C22 C7 113.2(2)
C2 C22 Br1 110.45(18)
C7 C22 Br1 110.42(18)
C2 C22 Br2 111.28(18)
C7 C22 Br2 102.33(18)
Br1 C22 Br2 108.84(12)
C10 C9 C4 115.3(2)
C10 C9 C3 124.9(2)
C4 C9 C3 119.6(2)
O3 C10 C9 125.5(2)
O3 C10 C7 113.4(2)
C9 C10 C7 121.2(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C22 1.932(2)
Br2 C22 1.958(3)
O1 C1 1.207(3)
O2 C1 1.328(3)
O2 C11 1.458(3)
O3 C10 1.318(3)
O3 B 1.471(3)
F2 B 1.367(3)
F1 B 1.364(4)
O6 C4 1.294(3)
O6 C12 1.459(3)
O7 C7 1.200(3)
C1 C2 1.526(4)
C2 C22 1.525(4)
C2 C3 1.546(3)
C3 C9 1.497(4)
C4 O8 1.269(3)
C4 C9 1.440(4)
O8 B 1.533(4)
C7 C10 1.507(4)
C7 C22 1.528(4)
C9 C10 1.360(4)
