#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:08:28 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201955 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/00/80/2008014.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_2008014
loop_
_publ_author_name
'Boese, Roland'
'Roth, Wolfgang R.'
'Bläser, Dieter'
'Latz, Rüdiger'
'Bäumen, Anja'
_publ_section_title
;
 2,2,3,3-Tetrachloro-1,4-diphenylbicyclo[2.2.0]hexane, a Strained
 Bicyclic System
;
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              IUC9800072
_journal_paper_doi               10.1107/S0108270198099107
_journal_volume                  54
_journal_year                    1998
_chemical_formula_sum            'C18 H14 Cl4'
_chemical_formula_weight         372.09
_chemical_name_systematic
;
 1,4-Diphenyl-2,2,3,3-tetrachlorbicyclo[2.2.0]hexane
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.58720(10)
_cell_length_b                   11.1006(2)
_cell_length_c                   19.66480(10)
_cell_measurement_reflns_used    8192
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.26
_cell_measurement_theta_min      2.77
_cell_volume                     1656.22(4)
_computing_cell_refinement       'SAINT Vers.4.050 (Siemens, 1995)'
_computing_data_collection       'SMART Vers.4.209 (Siemens, 1995)'
_computing_data_reduction        'SAINT Vers.4.050 (Siemens, 1995)'
_computing_molecular_graphics    'SHELXL-97 (Sheldrick, 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.794
_diffrn_measured_fraction_theta_max 0.794
_diffrn_measurement_device_type
'Siemens SMART CCD area detector system three axis platform'
_diffrn_measurement_method
;
Full-sphere data collection in omega at 0.3° scan width,
120 frames, phi = 0°,  in phi at 0.3° scan width four runs with 600 frames,
omega = 135, 143, 156, 169 (°).
;
_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  0.024
_diffrn_reflns_av_sigmaI/netI    0.0182
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -2
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            14665
_diffrn_reflns_reduction_process ' ?'
_diffrn_reflns_theta_full        28.26
_diffrn_reflns_theta_max         28.26
_diffrn_reflns_theta_min         2.77
_exptl_absorpt_coefficient_mu    0.707
_exptl_absorpt_correction_T_max  0.854
_exptl_absorpt_correction_T_min  0.751
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'Siemens SADABS program multi-scan (Blessing, 1995)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.492
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.456
_refine_diff_density_min         -0.208
_refine_ls_abs_structure_details 'Flack (1983)'
_refine_ls_abs_structure_Flack   -0.03(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3311
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.094
_refine_ls_R_factor_all          0.039
_refine_ls_R_factor_gt           0.036
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
w = 1/[σ²(Fo²)+(0.0554P)²+0.2665P] where P = (Fo²+2Fc²)/3'
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.092
_reflns_number_gt                3073
_reflns_number_total             3311
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            qa0070.cif
_cod_data_source_block           qa0070
_cod_database_code               2008014
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'
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_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
Cl1 0.17853(7) -0.14484(7) 0.91785(3) 0.05358(18) Uani d . 1 . . Cl
Cl2 0.73996(8) -0.15867(7) 0.93151(4) 0.05877(19) Uani d . 1 . . Cl
Cl3 0.47238(9) -0.03935(6) 1.00574(3) 0.05400(17) Uani d . 1 . . Cl
Cl4 0.43375(10) -0.31622(6) 0.87182(4) 0.0617(2) Uani d . 1 . . Cl
C1 0.4170(3) -0.0772(2) 0.82009(11) 0.0365(5) Uani d . 1 . . C
C2 0.3922(3) -0.1600(2) 0.88189(12) 0.0410(5) Uani d . 1 . . C
C3 0.5344(3) -0.0840(2) 0.92277(11) 0.0412(5) Uani d . 1 . . C
C4 0.5275(3) 0.0169(2) 0.86525(11) 0.0382(5) Uani d . 1 . . C
C5 0.6801(3) 0.0076(2) 0.81363(13) 0.0477(6) Uani d . 1 . . C
H5A 0.6868 0.0757 0.7836 0.057 Uiso d R 1 . . H
H5B 0.7925 -0.0084 0.8341 0.057 Uiso d R 1 . . H
C6 0.5933(3) -0.1023(2) 0.78005(13) 0.0466(6) Uani d . 1 . . C
H6A 0.6484 -0.1767 0.7929 0.056 Uiso d R 1 . . H
H6B 0.5822 -0.0967 0.7315 0.056 Uiso d R 1 . . H
C7 0.4744(3) 0.1407(2) 0.88826(12) 0.0419(5) Uani d . 1 . . C
C8 0.6024(4) 0.2297(3) 0.89202(15) 0.0567(7) Uani d . 1 . . C
H8 0.7210 0.2114 0.8785 0.068 Uiso d R 1 . . H
C9 0.5582(5) 0.3456(3) 0.91623(17) 0.0705(9) Uani d . 1 . . C
H9 0.6467 0.4073 0.9178 0.085 Uiso d R 1 . . H
C10 0.3907(5) 0.3703(3) 0.93688(17) 0.0719(9) Uani d . 1 . . C
H10 0.3612 0.4488 0.9540 0.086 Uiso d R 1 . . H
C11 0.2620(4) 0.2830(3) 0.93290(15) 0.0618(7) Uani d . 1 . . C
H11 0.1442 0.3016 0.9473 0.074 Uiso d R 1 . . H
C12 0.3027(3) 0.1696(3) 0.90881(13) 0.0508(6) Uani d . 1 . . C
H12 0.2120 0.1095 0.9059 0.061 Uiso d R 1 . . H
C13 0.2636(3) -0.0508(2) 0.77443(12) 0.0396(5) Uani d . 1 . . C
C14 0.2399(3) 0.0629(2) 0.74687(13) 0.0497(6) Uani d . 1 . . C
H14 0.3177 0.1268 0.7603 0.060 Uiso d R 1 . . H
C15 0.1067(4) 0.0850(3) 0.69948(15) 0.0588(7) Uani d . 1 . . C
H15 0.0919 0.1642 0.6806 0.071 Uiso d R 1 . . H
C16 -0.0047(3) -0.0076(3) 0.68062(14) 0.0574(7) Uani d . 1 . . C
H16 -0.0983 0.0070 0.6488 0.069 Uiso d R 1 . . H
C17 0.0186(3) -0.1211(3) 0.70744(14) 0.0539(6) Uani d . 1 . . C
H17 -0.0584 -0.1853 0.6937 0.065 Uiso d R 1 . . H
C18 0.1525(3) -0.1435(3) 0.75373(13) 0.0487(6) Uani d . 1 . . C
H18 0.1687 -0.2232 0.7717 0.058 Uiso d R 1 . . H
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'
Cl Cl 0.1484 0.1585 '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
C13 C1 C2 119.75(18)
C13 C1 C6 113.20(18)
C2 C1 C6 113.18(18)
C13 C1 C4 127.5(2)
C2 C1 C4 90.88(17)
C6 C1 C4 87.02(15)
C1 C2 C3 89.98(17)
C1 C2 Cl4 118.37(17)
C3 C2 Cl4 117.10(16)
C1 C2 Cl1 111.73(15)
C3 C2 Cl1 111.60(15)
Cl4 C2 Cl1 107.39(13)
C2 C3 C4 89.53(16)
C2 C3 Cl3 115.79(15)
C4 C3 Cl3 116.73(17)
C2 C3 Cl2 113.43(16)
C4 C3 Cl2 115.22(15)
Cl3 C3 Cl2 105.97(12)
C7 C4 C5 117.4(2)
C7 C4 C3 115.97(19)
C5 C4 C3 113.33(19)
C7 C4 C1 128.39(19)
C5 C4 C1 89.11(17)
C3 C4 C1 87.29(16)
C6 C5 C4 90.82(17)
C5 C6 C1 90.51(18)
C8 C7 C12 118.2(2)
C8 C7 C4 118.7(2)
C12 C7 C4 123.1(2)
C7 C8 C9 120.0(3)
C10 C9 C8 120.4(3)
C9 C10 C11 120.2(3)
C10 C11 C12 120.1(3)
C11 C12 C7 121.1(3)
C14 C13 C18 118.7(2)
C14 C13 C1 120.9(2)
C18 C13 C1 120.1(2)
C13 C14 C15 121.0(3)
C16 C15 C14 119.4(3)
C17 C16 C15 119.9(2)
C16 C17 C18 120.6(3)
C17 C18 C13 120.2(3)
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
Cl1 C2 . 1.777(2) ?
Cl2 C3 . 1.775(2) ?
Cl3 C3 . 1.769(2) ?
Cl4 C2 . 1.774(3) ?
C1 C13 . 1.499(3) ?
C1 C2 . 1.535(3) ?
C1 C6 . 1.577(3) ?
C1 C4 . 1.607(3) ?
C2 C3 . 1.588(3) ?
C3 C4 . 1.592(3) ?
C4 C7 . 1.502(3) ?
C4 C5 . 1.543(3) ?
C5 C6 . 1.535(4) ?
C7 C8 . 1.388(3) ?
C7 C12 . 1.401(3) ?
C8 C9 . 1.412(4) ?
C9 C10 . 1.362(5) ?
C10 C11 . 1.378(5) ?
C11 C12 . 1.380(4) ?
C13 C14 . 1.385(3) ?
C13 C18 . 1.391(3) ?
C14 C15 . 1.397(4) ?
C15 C16 . 1.382(4) ?
C16 C17 . 1.378(4) ?
C17 C18 . 1.387(3) ?
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
C13 C1 C2 C3 -146.9(2)
C6 C1 C2 C3 75.6(2)
C4 C1 C2 C3 -11.58(16)
C13 C1 C2 Cl4 92.0(2)
C6 C1 C2 Cl4 -45.6(2)
C4 C1 C2 Cl4 -132.74(16)
C13 C1 C2 Cl1 -33.5(3)
C6 C1 C2 Cl1 -171.11(16)
C4 C1 C2 Cl1 101.76(16)
C1 C2 C3 C4 11.69(16)
Cl4 C2 C3 C4 133.93(16)
Cl1 C2 C3 C4 -101.76(17)
C1 C2 C3 Cl3 131.40(16)
Cl4 C2 C3 Cl3 -106.36(17)
Cl1 C2 C3 Cl3 18.0(2)
C1 C2 C3 Cl2 -105.75(16)
Cl4 C2 C3 Cl2 16.5(2)
Cl1 C2 C3 Cl2 140.80(13)
C2 C3 C4 C7 120.8(2)
Cl3 C3 C4 C7 1.9(3)
Cl2 C3 C4 C7 -123.40(19)
C2 C3 C4 C5 -99.03(19)
Cl3 C3 C4 C5 142.09(17)
Cl2 C3 C4 C5 16.8(3)
C2 C3 C4 C1 -11.17(15)
Cl3 C3 C4 C1 -130.05(16)
Cl2 C3 C4 C1 104.66(16)
C13 C1 C4 C7 19.7(3)
C2 C1 C4 C7 -109.9(2)
C6 C1 C4 C7 136.9(2)
C13 C1 C4 C5 -105.4(2)
C2 C1 C4 C5 124.97(17)
C6 C1 C4 C5 11.81(18)
C13 C1 C4 C3 141.2(2)
C2 C1 C4 C3 11.56(15)
C6 C1 C4 C3 -101.60(17)
C7 C4 C5 C6 -145.9(2)
C3 C4 C5 C6 74.5(2)
C1 C4 C5 C6 -12.11(18)
C4 C5 C6 C1 12.35(19)
C13 C1 C6 C5 118.0(2)
C2 C1 C6 C5 -101.5(2)
C4 C1 C6 C5 -11.86(18)
C5 C4 C7 C8 -31.6(3)
C3 C4 C7 C8 106.9(2)
C1 C4 C7 C8 -144.5(2)
C5 C4 C7 C12 151.1(2)
C3 C4 C7 C12 -70.4(3)
C1 C4 C7 C12 38.2(4)
C12 C7 C8 C9 0.2(4)
C4 C7 C8 C9 -177.3(3)
C7 C8 C9 C10 0.9(5)
C8 C9 C10 C11 -1.4(5)
C9 C10 C11 C12 0.9(5)
C10 C11 C12 C7 0.2(4)
C8 C7 C12 C11 -0.7(4)
C4 C7 C12 C11 176.6(2)
C2 C1 C13 C14 141.7(2)
C6 C1 C13 C14 -80.7(3)
C4 C1 C13 C14 24.2(3)
C2 C1 C13 C18 -44.7(3)
C6 C1 C13 C18 92.9(3)
C4 C1 C13 C18 -162.2(2)
C18 C13 C14 C15 0.4(4)
C1 C13 C14 C15 174.1(2)
C13 C14 C15 C16 1.0(4)
C14 C15 C16 C17 -1.4(4)
C15 C16 C17 C18 0.5(4)
C16 C17 C18 C13 0.9(4)
C14 C13 C18 C17 -1.3(4)
C1 C13 C18 C17 -175.1(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21183274
