#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:47:24 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178444 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/65/4026585.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_4026585
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         'C13 H14 Br2'
_chemical_formula_sum            'C13 H14 Br2'
_chemical_formula_weight         330.06
_chemical_name_systematic
; 
12,12-Dibromo-7-methylenetetracyclo[6.3.1.0^1,8^.0^2,6^]dodec-
2(6)-ene
;
_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                 102.036(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.1835(3)
_cell_length_b                   9.9975(4)
_cell_length_c                   14.7884(6)
_cell_measurement_reflns_used    711
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.12
_cell_measurement_theta_min      2.57
_cell_volume                     1183.31(8)
_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  0.0817
_diffrn_reflns_av_sigmaI/netI    0.0448
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            37383
_diffrn_reflns_theta_full        30.04
_diffrn_reflns_theta_max         30.04
_diffrn_reflns_theta_min         2.48
_exptl_absorpt_coefficient_mu    6.814
_exptl_absorpt_correction_T_max  0.7269
_exptl_absorpt_correction_T_min  0.2807
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.853
_exptl_crystal_description       block
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.594
_refine_diff_density_min         -0.503
_refine_diff_density_rms         0.118
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         3457
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.004
_refine_ls_R_factor_all          0.0544
_refine_ls_R_factor_gt           0.0302
_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)+(0.0219P)²+1.1838P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0560
_refine_ls_wR_factor_ref         0.0625
_reflns_number_gt                2596
_reflns_number_total             3457
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo201308a_si_003.cif
_cod_data_source_block           kusu232
_cod_database_code               4026585
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 1.03971(3) 0.58803(3) 0.240118(19) 0.01909(8) Uani 1 1 d .
Br2 Br 1.10899(3) 0.86681(3) 0.16000(2) 0.02075(8) Uani 1 1 d .
C5 C 0.8354(3) 0.6892(3) 0.06066(17) 0.0128(5) Uani 1 1 d .
C4 C 0.7619(3) 0.7591(3) 0.13586(17) 0.0130(5) Uani 1 1 d .
C3 C 0.6484(3) 0.6600(3) 0.16849(17) 0.0140(5) Uani 1 1 d .
C2 C 0.6655(3) 0.5364(3) 0.11760(18) 0.0142(5) Uani 1 1 d .
C8 C 0.6803(3) 0.3236(3) 0.04659(19) 0.0194(6) Uani 1 1 d .
H8A H 0.7429 0.2423 0.0715 0.023 Uiso 1 1 calc R
H8B H 0.5880 0.2970 -0.0048 0.023 Uiso 1 1 calc R
C9 C 0.6093(3) 0.3949(3) 0.12404(19) 0.0182(6) Uani 1 1 d .
H9A H 0.4859 0.3888 0.1120 0.022 Uiso 1 1 calc R
H9B H 0.6564 0.3561 0.1855 0.022 Uiso 1 1 calc R
C6 C 0.9463(3) 0.7253(3) 0.15221(18) 0.0146(5) Uani 1 1 d .
C7 C 0.7982(3) 0.4242(3) 0.0116(2) 0.0213(6) Uani 1 1 d .
H7A H 0.9166 0.3967 0.0309 0.026 Uiso 1 1 calc R
H7B H 0.7695 0.4327 -0.0566 0.026 Uiso 1 1 calc R
C1 C 0.7658(3) 0.5517(3) 0.05734(18) 0.0135(5) Uani 1 1 d .
C10 C 0.7073(3) 0.8990(3) 0.10282(19) 0.0172(6) Uani 1 1 d .
H10A H 0.7804 0.9669 0.1396 0.021 Uiso 1 1 calc R
H10B H 0.5906 0.9156 0.1086 0.021 Uiso 1 1 calc R
C12 C 0.8277(3) 0.7854(3) -0.02037(18) 0.0160(5) Uani 1 1 d .
H12A H 0.7741 0.7421 -0.0793 0.019 Uiso 1 1 calc R
H12B H 0.9412 0.8151 -0.0247 0.019 Uiso 1 1 calc R
C13 C 0.5488(3) 0.6833(3) 0.22711(18) 0.0179(6) Uani 1 1 d .
H13A H 0.4768 0.6148 0.2404 0.021 Uiso 1 1 calc R
H13B H 0.5496 0.7684 0.2558 0.021 Uiso 1 1 calc R
C11 C 0.7219(5) 0.9047(3) 0.0012(2) 0.0346(8) Uani 1 1 d .
H11A H 0.7754 0.9898 -0.0110 0.042 Uiso 1 1 calc R
H11B H 0.6092 0.9011 -0.0393 0.042 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'
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
C1 C5 C6 114.0(2)
C1 C5 C12 127.1(2)
C6 C5 C12 118.2(2)
C1 C5 C4 103.9(2)
C6 C5 C4 59.66(16)
C12 C5 C4 108.8(2)
C3 C4 C6 117.6(2)
C3 C4 C10 123.3(2)
C6 C4 C10 118.3(2)
C3 C4 C5 107.0(2)
C6 C4 C5 59.18(16)
C10 C4 C5 108.6(2)
C13 C3 C2 128.2(2)
C13 C3 C4 126.7(2)
C2 C3 C4 105.0(2)
C1 C2 C3 112.4(2)
C1 C2 C9 112.9(2)
C3 C2 C9 134.4(2)
C7 C8 C9 107.5(2)
C7 C8 H8A 110.2
C9 C8 H8A 110.2
C7 C8 H8B 110.2
C9 C8 H8B 110.2
H8A C8 H8B 108.5
C2 C9 C8 102.6(2)
C2 C9 H9A 111.2
C8 C9 H9A 111.2
C2 C9 H9B 111.2
C8 C9 H9B 111.2
H9A C9 H9B 109.2
C5 C6 C4 61.16(16)
C5 C6 Br2 120.51(18)
C4 C6 Br2 119.84(18)
C5 C6 Br1 120.84(18)
C4 C6 Br1 120.40(18)
Br2 C6 Br1 108.00(12)
C1 C7 C8 102.7(2)
C1 C7 H7A 111.2
C8 C7 H7A 111.2
C1 C7 H7B 111.2
C8 C7 H7B 111.2
H7A C7 H7B 109.1
C2 C1 C5 111.6(2)
C2 C1 C7 113.3(2)
C5 C1 C7 134.6(2)
C4 C10 C11 105.8(2)
C4 C10 H10A 110.6
C11 C10 H10A 110.6
C4 C10 H10B 110.6
C11 C10 H10B 110.6
H10A C10 H10B 108.7
C5 C12 C11 105.0(2)
C5 C12 H12A 110.8
C11 C12 H12A 110.8
C5 C12 H12B 110.8
C11 C12 H12B 110.8
H12A C12 H12B 108.8
C3 C13 H13A 120.0
C3 C13 H13B 120.0
H13A C13 H13B 120.0
C10 C11 C12 109.5(2)
C10 C11 H11A 109.8
C12 C11 H11A 109.8
C10 C11 H11B 109.8
C12 C11 H11B 109.8
H11A C11 H11B 108.2
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C6 1.935(3)
Br2 C6 1.929(2)
C5 C1 1.485(4)
C5 C6 1.508(3)
C5 C12 1.527(3)
C5 C4 1.538(3)
C4 C3 1.505(3)
C4 C6 1.516(3)
C4 C10 1.517(4)
C3 C13 1.328(3)
C3 C2 1.469(4)
C2 C1 1.340(4)
C2 C9 1.496(4)
C8 C7 1.555(4)
C8 C9 1.560(4)
C8 H8A 0.9900
C8 H8B 0.9900
C9 H9A 0.9900
C9 H9B 0.9900
C7 C1 1.492(4)
C7 H7A 0.9900
C7 H7B 0.9900
C10 C11 1.534(4)
C10 H10A 0.9900
C10 H10B 0.9900
C12 C11 1.546(4)
C12 H12A 0.9900
C12 H12B 0.9900
C13 H13A 0.9500
C13 H13B 0.9500
C11 H11A 0.9900
C11 H11B 0.9900
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
C1 C5 C4 C3 -2.5(3)
C6 C5 C4 C3 -112.4(2)
C12 C5 C4 C3 135.4(2)
C1 C5 C4 C6 109.9(2)
C12 C5 C4 C6 -112.3(2)
C1 C5 C4 C10 -137.7(2)
C6 C5 C4 C10 112.4(2)
C12 C5 C4 C10 0.1(3)
C6 C4 C3 C13 122.7(3)
C10 C4 C3 C13 -46.7(4)
C5 C4 C3 C13 -173.7(3)
C6 C4 C3 C2 -60.4(3)
C10 C4 C3 C2 130.2(2)
C5 C4 C3 C2 3.3(3)
C13 C3 C2 C1 173.8(3)
C4 C3 C2 C1 -3.0(3)
C13 C3 C2 C9 -13.0(5)
C4 C3 C2 C9 170.2(3)
C1 C2 C9 C8 -5.8(3)
C3 C2 C9 C8 -178.9(3)
C7 C8 C9 C2 9.3(3)
C1 C5 C6 C4 -92.5(2)
C12 C5 C6 C4 96.3(2)
C1 C5 C6 Br2 157.95(18)
C12 C5 C6 Br2 -13.2(3)
C4 C5 C6 Br2 -109.6(2)
C1 C5 C6 Br1 17.6(3)
C12 C5 C6 Br1 -153.55(18)
C4 C5 C6 Br1 110.1(2)
C3 C4 C6 C5 94.2(2)
C10 C4 C6 C5 -95.8(3)
C3 C4 C6 Br2 -155.15(19)
C10 C4 C6 Br2 14.8(3)
C5 C4 C6 Br2 110.6(2)
C3 C4 C6 Br1 -16.6(3)
C10 C4 C6 Br1 153.35(19)
C5 C4 C6 Br1 -110.8(2)
C9 C8 C7 C1 -9.5(3)
C3 C2 C1 C5 1.5(3)
C9 C2 C1 C5 -173.2(2)
C3 C2 C1 C7 174.4(2)
C9 C2 C1 C7 -0.3(3)
C6 C5 C1 C2 63.3(3)
C12 C5 C1 C2 -126.5(3)
C4 C5 C1 C2 0.7(3)
C6 C5 C1 C7 -107.5(3)
C12 C5 C1 C7 62.7(4)
C4 C5 C1 C7 -170.1(3)
C8 C7 C1 C2 6.3(3)
C8 C7 C1 C5 177.0(3)
C3 C4 C10 C11 -117.3(3)
C6 C4 C10 C11 73.4(3)
C5 C4 C10 C11 9.0(3)
C1 C5 C12 C11 116.1(3)
C6 C5 C12 C11 -74.1(3)
C4 C5 C12 C11 -9.1(3)
C4 C10 C11 C12 -15.0(3)
C5 C12 C11 C10 14.9(3)
