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#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/61/2206137.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2206137
loop_
_publ_author_name
'Jones, Peter G.'
'Kämpen, Jan'
'Bubenitschek, Peter'
'Hopf, Henning'
_publ_section_title
;
 1,4-Bis(dibromomethylidene)cyclohexane: crystal packing with
 Br···Br and Br···π contacts
;
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2179
_journal_page_last               o2180
_journal_paper_doi               10.1107/S1600536805018374
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C8 H8 Br4'
_chemical_formula_moiety         'C8 H8 Br4'
_chemical_formula_sum            'C8 H8 Br4'
_chemical_formula_weight         423.78
_chemical_name_systematic
;
1,4-Bis(dibromomethylidene)cyclohexane
;
_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                 102.783(12)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   6.6033(10)
_cell_length_b                   12.3957(18)
_cell_length_c                   6.7152(10)
_cell_measurement_reflns_used    62
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      12.5
_cell_measurement_theta_min      3.5
_cell_volume                     536.03(14)
_computing_cell_refinement       XSCANS
_computing_data_collection       'XSCANS (Fait, 1991)'
_computing_data_reduction        XSCANS
_computing_molecular_graphics    'XP5 (Siemens, 1994)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.957
_diffrn_measured_fraction_theta_max 0.957
_diffrn_measurement_device_type  'Siemens P4'
_diffrn_measurement_method       ω
_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  0.0755
_diffrn_reflns_av_sigmaI/netI    0.0614
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            973
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.29
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 247
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    14.961
_exptl_absorpt_correction_T_max  0.95
_exptl_absorpt_correction_T_min  0.30
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(XEMP; Siemens, 1994)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.626
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       tablet
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.964
_refine_diff_density_min         -0.713
_refine_ls_extinction_coef       0.043(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.126
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     56
_refine_ls_number_reflns         901
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.123
_refine_ls_R_factor_all          0.0652
_refine_ls_R_factor_gt           0.0415
_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)+(0.0640P)²] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0976
_refine_ls_wR_factor_ref         0.1051
_reflns_number_gt                738
_reflns_number_total             901
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt6681.cif
_cod_data_source_block           2
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2206137
_cod_database_fobs_code          2206137
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_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_type_symbol
Br1 0.59085(13) 0.27787(7) 0.46164(13) 0.0310(3) Uani d . 1 Br
Br2 0.18311(11) 0.41201(7) 0.43723(12) 0.0272(3) Uani d . 1 Br
C1 0.4057(11) 0.3809(6) 0.3106(11) 0.0200(16) Uani d U 1 C
C2 0.4294(11) 0.4255(6) 0.1393(12) 0.0207(16) Uani d U 1 C
C3 0.2849(11) 0.5080(7) 0.0242(11) 0.0247(16) Uani d U 1 C
H3A 0.1884 0.5320 0.1091 0.030 Uiso calc R 1 H
H3B 0.2012 0.4747 -0.1013 0.030 Uiso calc R 1 H
C4 0.3993(11) 0.6060(7) -0.0343(12) 0.0269(17) Uani d U 1 C
H4A 0.2990 0.6531 -0.1263 0.032 Uiso calc R 1 H
H4B 0.4595 0.6479 0.0903 0.032 Uiso calc R 1 H
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
Br1 0.0337(5) 0.0274(5) 0.0331(5) 0.0081(4) 0.0100(4) 0.0113(4)
Br2 0.0293(5) 0.0273(5) 0.0287(5) 0.0018(3) 0.0146(3) 0.0020(3)
C1 0.021(3) 0.018(4) 0.021(4) 0.000(3) 0.006(3) -0.003(3)
C2 0.017(3) 0.020(4) 0.024(4) 0.002(3) 0.002(3) -0.001(3)
C3 0.021(3) 0.027(4) 0.026(4) 0.006(3) 0.006(3) 0.004(3)
C4 0.026(4) 0.025(4) 0.030(4) 0.009(3) 0.009(3) 0.004(4)
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 C1 Br2 . . 124.1(6) y
C2 C1 Br1 . . 124.2(6) y
Br2 C1 Br1 . . 111.7(4) y
C1 C2 C3 . . 123.7(7) y
C1 C2 C4 . 3_665 123.0(7) y
C3 C2 C4 . 3_665 113.2(6) y
C2 C3 C4 . . 112.5(6) ?
C2 C3 H3A . . 109.1 ?
C4 C3 H3A . . 109.1 ?
C2 C3 H3B . . 109.1 ?
C4 C3 H3B . . 109.1 ?
H3A C3 H3B . . 107.8 ?
C2 C4 C3 3_665 . 112.3(7) ?
C2 C4 H4A 3_665 . 109.2 ?
C3 C4 H4A . . 109.2 ?
C2 C4 H4B 3_665 . 109.2 ?
C3 C4 H4B . . 109.2 ?
H4A C4 H4B . . 107.9 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Br1 C1 . 1.899(7) y
Br2 C1 . 1.894(7) y
C1 C2 . 1.316(11) y
C2 C3 . 1.492(11) ?
C2 C4 3_665 1.510(10) ?
C3 C4 . 1.527(11) ?
C3 H3A . 0.9900 ?
C3 H3B . 0.9900 ?
C4 H4A . 0.9900 ?
C4 H4B . 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_site_symmetry_1
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
Br2 C1 C2 C3 . . . 1.0(12) ?
Br1 C1 C2 C3 . . . -178.8(6) ?
Br2 C1 C2 C4 . . 3_665 -175.9(6) ?
Br1 C1 C2 C4 . . 3_665 4.3(11) ?
C1 C2 C3 C4 . . . 131.4(8) ?
C4 C2 C3 C4 3_665 . . -51.4(10) y
C2 C3 C4 C2 . . 3_665 50.9(10) y
C3 C4 C2 C3 . 3:665 3_665 -51.3(10) y
