#------------------------------------------------------------------------------
#$Date: 2016-02-14 05:40:26 +0100 (dom 14 de feb de 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/65/4026584.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_4026584
loop_
_publ_author_name
'Kuan-Jen Su'
'Mirjana Pačar'
'Jean-Luc Mieusset'
'Vladimir B. Arion'
'Udo H. Brinker'
_publ_section_title
;
 Quest for Even Higher Stabilized Foiled Carbenes
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7491
_journal_page_last               7496
_journal_paper_doi               10.1021/jo201308a
_journal_volume                  76
_journal_year                    2011
_chemical_formula_moiety         'C12 H12 Br2 O'
_chemical_formula_sum            'C12 H12 Br2 O'
_chemical_formula_weight         332.04
_chemical_name_systematic
; 
12,12-Dibromotetracyclo[6.3.1.0^1,8^.0^2,6^]dodec-2(6)-en-7-one 
;
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   7.5320(4)
_cell_length_b                   15.8313(8)
_cell_length_c                   18.9055(10)
_cell_measurement_reflns_used    1463
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.16
_cell_measurement_theta_min      2.18
_cell_volume                     2254.3(2)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0885
_diffrn_reflns_av_sigmaI/netI    0.0278
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            48188
_diffrn_reflns_theta_full        25.73
_diffrn_reflns_theta_max         25.73
_diffrn_reflns_theta_min         2.57
_exptl_absorpt_coefficient_mu    7.161
_exptl_absorpt_correction_T_max  0.1884
_exptl_absorpt_correction_T_min  0.1409
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.957
_exptl_crystal_description       block
_exptl_crystal_F_000             1296
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.35
_refine_diff_density_max         0.512
_refine_diff_density_min         -0.453
_refine_diff_density_rms         0.096
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         2150
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0427
_refine_ls_R_factor_gt           0.0226
_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)+(0.0198P)²+4.7460P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0475
_refine_ls_wR_factor_ref         0.0551
_reflns_number_gt                1642
_reflns_number_total             2150
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo201308a_si_002.cif
_cod_data_source_block           kusu225
_cod_original_sg_symbol_Hall     '-P2ac 2ab'
_cod_database_code               4026584
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_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 1.10242(4) 0.683503(19) 0.491558(16) 0.01493(10) Uani 1 1 d .
Br2 Br 0.77250(4) 0.562513(19) 0.485399(16) 0.01407(9) Uani 1 1 d .
O1 O 1.2723(3) 0.57365(13) 0.66588(12) 0.0171(5) Uani 1 1 d .
C12 C 0.9245(4) 0.62600(19) 0.54753(16) 0.0091(6) Uani 1 1 d .
C11 C 0.8530(4) 0.66620(18) 0.61398(16) 0.0081(6) Uani 1 1 d .
C6 C 1.1475(4) 0.61857(19) 0.65044(16) 0.0106(7) Uani 1 1 d .
C2 C 1.1271(4) 0.71002(19) 0.66083(16) 0.0096(7) Uani 1 1 d .
C8 C 0.8701(4) 0.51482(19) 0.64766(17) 0.0114(7) Uani 1 1 d .
H8A H 0.9157 0.4986 0.6949 0.014 Uiso 1 1 calc R
H8B H 0.8795 0.4654 0.6157 0.014 Uiso 1 1 calc R
C5 C 0.9477(4) 0.83023(18) 0.64526(17) 0.0108(7) Uani 1 1 d .
H5A H 0.8363 0.8471 0.6692 0.013 Uiso 1 1 calc R
H5B H 0.9516 0.8560 0.5976 0.013 Uiso 1 1 calc R
C7 C 0.9743(4) 0.58861(18) 0.61840(16) 0.0085(6) Uani 1 1 d .
C1 C 0.9657(4) 0.73616(18) 0.64167(15) 0.0085(6) Uani 1 1 d .
C10 C 0.6692(4) 0.64179(19) 0.64021(17) 0.0115(7) Uani 1 1 d .
H10A H 0.5781 0.6562 0.6044 0.014 Uiso 1 1 calc R
H10B H 0.6409 0.6720 0.6846 0.014 Uiso 1 1 calc R
C3 C 1.2481(4) 0.78178(19) 0.68016(18) 0.0132(7) Uani 1 1 d .
H3A H 1.3340 0.7940 0.6419 0.016 Uiso 1 1 calc R
H3B H 1.3135 0.7701 0.7245 0.016 Uiso 1 1 calc R
C4 C 1.1132(4) 0.85488(19) 0.68966(17) 0.0133(7) Uani 1 1 d .
H4A H 1.1642 0.9087 0.6725 0.016 Uiso 1 1 calc R
H4B H 1.0810 0.8614 0.7401 0.016 Uiso 1 1 calc R
C9 C 0.6739(4) 0.54503(19) 0.65304(18) 0.0124(7) Uani 1 1 d .
H9A H 0.6004 0.5158 0.6172 0.015 Uiso 1 1 calc R
H9B H 0.6256 0.5318 0.7005 0.015 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
C11 C12 C7 61.02(19)
C11 C12 Br2 121.1(2)
C7 C12 Br2 119.0(2)
C11 C12 Br1 120.3(2)
C7 C12 Br1 119.8(2)
Br2 C12 Br1 108.91(15)
C1 C11 C12 113.7(3)
C1 C11 C10 126.4(3)
C12 C11 C10 119.3(3)
C1 C11 C7 103.7(2)
C12 C11 C7 59.62(19)
C10 C11 C7 108.7(2)
O1 C6 C2 128.7(3)
O1 C6 C7 125.4(3)
C2 C6 C7 105.8(3)
C1 C2 C6 111.4(3)
C1 C2 C3 112.6(3)
C6 C2 C3 135.6(3)
C7 C8 C9 106.2(2)
C1 C5 C4 101.6(3)
C12 C7 C8 119.9(3)
C12 C7 C6 116.5(3)
C8 C7 C6 122.9(3)
C12 C7 C11 59.35(19)
C8 C7 C11 109.2(2)
C6 C7 C11 106.5(2)
C2 C1 C11 112.6(3)
C2 C1 C5 112.3(3)
C11 C1 C5 134.7(3)
C11 C10 C9 106.3(2)
C2 C3 C4 101.2(2)
C3 C4 C5 106.0(2)
C10 C9 C8 108.3(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C12 1.935(3)
Br2 C12 1.924(3)
O1 C6 1.214(4)
C12 C11 1.508(4)
C12 C7 1.512(4)
C11 C1 1.491(4)
C11 C10 1.520(4)
C11 C7 1.533(4)
C6 C2 1.469(4)
C6 C7 1.514(4)
C2 C1 1.334(4)
C2 C3 1.502(4)
C8 C7 1.512(4)
C8 C9 1.557(4)
C5 C1 1.497(4)
C5 C4 1.553(4)
C10 C9 1.551(4)
C3 C4 1.551(4)
