#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/11/2201102.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_2201102
loop_
_publ_author_name
'Barnes, John C.'
'Chudek, John A.'
_publ_section_title
;
 cis-1,2-Dibromo-1,2-diphenylethene--diphenylethyne (2/1)
;
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o703
_journal_page_last               o705
_journal_paper_doi               10.1107/S160053680200942X
_journal_volume                  58
_journal_year                    2002
_chemical_formula_iupac          'C14 H10 Br2, 0.5C14 H10'
_chemical_formula_moiety         'C14 H10 Br2, 0.5C14 H10'
_chemical_formula_sum            'C42 H30 Br4'
_chemical_formula_weight         854.30
_chemical_melting_point          69.5(15)
_chemical_name_common
;
Cis-1,2-dibromostilbene, diphenylacetylene (2:1)
;
_chemical_name_systematic
;
Cis-1,2-dibromo-1,2-diphenylethene, diphenylethyne (2:1)
;
_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                 104.037(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   14.8445(5)
_cell_length_b                   5.7702(3)
_cell_length_c                   20.741(9)
_cell_measurement_reflns_used    13506
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.10
_cell_measurement_theta_min      1.02
_cell_volume                     1723.5(8)
_computing_cell_refinement       'DENZO and COLLECT'
_computing_data_collection
;
DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998)
;
_computing_data_reduction        'DENZO and COLLECT'
_computing_molecular_graphics    'PLATON (Spek, 1999) '
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device_type  'Enraf--Nonius KappaCCD area-detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enraf--Nonius FR591 rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1029
_diffrn_reflns_av_sigmaI/netI    0.0893
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            11791
_diffrn_reflns_theta_full        27.10
_diffrn_reflns_theta_max         27.10
_diffrn_reflns_theta_min         2.83
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.700
_exptl_absorpt_correction_T_max  0.999
_exptl_absorpt_correction_T_min  0.946
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SORTAV; Blessing, 1995)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.646
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             844
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.760
_refine_diff_density_min         -0.953
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3718
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0880
_refine_ls_R_factor_gt           0.0554
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0826P)²] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1305
_refine_ls_wR_factor_ref         0.1482
_reflns_number_gt                2614
_reflns_number_total             3718
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cm6007.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '68 -71' was changed to '69.5(15)' -
the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 

The following automatic conversions were performed:

'_chemical_melting_point' value '68 -71' was changed to '69.5(15)' -
the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2201102
_cod_database_fobs_code          2201102
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_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
Br1 0.55860(4) 0.41738(10) 0.08283(2) 0.0458(2) Uani d . 1 . . Br
Br2 0.39224(3) 0.74326(8) 0.11248(2) 0.03678(19) Uani d . 1 . . Br
C1 0.5219(3) 0.3848(8) 0.1643(2) 0.0270(9) Uani d . 1 . . C
C2 0.4530(3) 0.5159(8) 0.1751(2) 0.0268(9) Uani d . 1 . . C
C3 0.5766(3) 0.2153(8) 0.2110(2) 0.0268(10) Uani d . 1 . . C
C4 0.6070(3) 0.0098(8) 0.1873(2) 0.0293(10) Uani d . 1 . . C
H4 0.5929 -0.0190 0.1409 0.038 Uiso calc R 1 . . H
C5 0.6576(3) -0.1518(8) 0.2308(2) 0.0303(10) Uani d . 1 . . C
H5 0.6764 -0.2925 0.2141 0.039 Uiso calc R 1 . . H
C6 0.6808(3) -0.1085(8) 0.2987(2) 0.0309(10) Uani d . 1 . . C
H6 0.7164 -0.2179 0.3286 0.040 Uiso calc R 1 . . H
C7 0.6518(3) 0.0947(8) 0.3226(2) 0.0296(10) Uani d . 1 . . C
H7 0.6670 0.1242 0.3690 0.038 Uiso calc R 1 . . H
C8 0.6005(3) 0.2562(7) 0.2790(2) 0.0247(9) Uani d . 1 . . C
H8 0.5816 0.3963 0.2959 0.032 Uiso calc R 1 . . H
C9 0.4140(3) 0.5057(8) 0.2344(2) 0.0277(9) Uani d . 1 . . C
C10 0.3636(3) 0.3103(8) 0.2446(2) 0.0307(10) Uani d . 1 . . C
H10 0.3551 0.1841 0.2142 0.040 Uiso calc R 1 . . H
C11 0.3260(3) 0.3032(9) 0.2996(2) 0.0365(11) Uani d . 1 . . C
H11 0.2906 0.1725 0.3065 0.047 Uiso calc R 1 . . H
C12 0.3394(3) 0.4827(9) 0.3440(2) 0.0342(11) Uani d . 1 . . C
H12 0.3149 0.4740 0.3822 0.044 Uiso calc R 1 . . H
C13 0.3885(3) 0.6765(9) 0.3335(2) 0.0323(10) Uani d . 1 . . C
H13 0.3965 0.8017 0.3641 0.042 Uiso calc R 1 . . H
C14 0.4259(3) 0.6900(8) 0.2792(2) 0.0297(10) Uani d . 1 . . C
H14 0.4595 0.8239 0.2723 0.039 Uiso calc R 1 . . H
C21 0.0314(3) 0.4395(8) -0.0025(2) 0.0298(10) Uani d . 1 . . C
C22 0.1070(3) 0.2943(8) -0.0099(2) 0.0272(9) Uani d . 1 . . C
C23 0.1989(3) 0.3597(9) 0.0163(2) 0.0327(10) Uani d . 1 . . C
H23 0.2122 0.5010 0.0402 0.042 Uiso calc R 1 . . H
C24 0.2706(3) 0.2210(9) 0.0078(3) 0.0388(12) Uani d . 1 . . C
H24 0.3332 0.2675 0.0253 0.050 Uiso calc R 1 . . H
C25 0.2511(4) 0.0119(9) -0.0267(3) 0.0402(12) Uani d . 1 . . C
H25 0.3004 -0.0831 -0.0332 0.052 Uiso calc R 1 . . H
C26 0.1613(4) -0.0558(8) -0.0508(2) 0.0391(12) Uani d . 1 . . C
H26 0.1485 -0.1998 -0.0734 0.051 Uiso calc R 1 . . H
C27 0.0886(3) 0.0822(8) -0.0430(2) 0.0330(10) Uani d . 1 . . C
H27 0.0263 0.0330 -0.0601 0.043 Uiso calc 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'
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
_geom_angle_publ_flag
C2 C1 C3 . 126.1(4) yes
C2 C1 Br1 . 119.2(3) yes
C3 C1 Br1 . 114.7(3) yes
C1 C2 C9 . 125.9(4) yes
C1 C2 Br2 . 122.0(3) yes
C9 C2 Br2 . 112.1(3) yes
C8 C3 C4 . 118.4(4) ?
C8 C3 C1 . 121.3(4) ?
C4 C3 C1 . 120.3(4) ?
C5 C4 C3 . 120.8(4) ?
C5 C4 H4 . 119.6 ?
C3 C4 H4 . 119.6 ?
C4 C5 C6 . 120.1(4) ?
C4 C5 H5 . 120.0 ?
C6 C5 H5 . 120.0 ?
C7 C6 C5 . 119.6(4) ?
C7 C6 H6 . 120.2 ?
C5 C6 H6 . 120.2 ?
C6 C7 C8 . 120.4(4) ?
C6 C7 H7 . 119.8 ?
C8 C7 H7 . 119.8 ?
C3 C8 C7 . 120.7(4) ?
C3 C8 H8 . 119.6 ?
C7 C8 H8 . 119.6 ?
C14 C9 C10 . 119.9(4) ?
C14 C9 C2 . 120.8(4) ?
C10 C9 C2 . 119.3(4) ?
C11 C10 C9 . 119.0(4) ?
C11 C10 H10 . 120.5 ?
C9 C10 H10 . 120.5 ?
C12 C11 C10 . 120.6(5) ?
C12 C11 H11 . 119.7 ?
C10 C11 H11 . 119.7 ?
C11 C12 C13 . 120.2(4) ?
C11 C12 H12 . 119.9 ?
C13 C12 H12 . 119.9 ?
C14 C13 C12 . 120.6(5) ?
C14 C13 H13 . 119.7 ?
C12 C13 H13 . 119.7 ?
C13 C14 C9 . 119.5(4) ?
C13 C14 H14 . 120.2 ?
C9 C14 H14 . 120.2 ?
C21 C21 C22 3_565 178.8(6) yes
C23 C22 C27 . 119.0(4) ?
C23 C22 C21 . 121.1(4) ?
C27 C22 C21 . 119.9(4) ?
C24 C23 C22 . 120.5(5) ?
C24 C23 H23 . 119.8 ?
C22 C23 H23 . 119.8 ?
C23 C24 C25 . 119.8(5) ?
C23 C24 H24 . 120.1 ?
C25 C24 H24 . 120.1 ?
C26 C25 C24 . 120.0(4) ?
C26 C25 H25 . 120.0 ?
C24 C25 H25 . 120.0 ?
C25 C26 C27 . 120.9(5) ?
C25 C26 H26 . 119.5 ?
C27 C26 H26 . 119.5 ?
C26 C27 C22 . 119.8(5) ?
C26 C27 H27 . 120.1 ?
C22 C27 H27 . 120.1 ?
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 . 1.907(4) yes
Br2 C2 . 1.912(4) yes
C1 C2 . 1.334(6) yes
C1 C3 . 1.474(6) yes
C2 C9 . 1.481(6) ?
C3 C8 . 1.388(6) ?
C3 C4 . 1.400(6) ?
C4 C5 . 1.384(7) ?
C4 H4 . 0.9500 ?
C5 C6 . 1.390(7) ?
C5 H5 . 0.9500 ?
C6 C7 . 1.381(7) ?
C6 H6 . 0.9500 ?
C7 C8 . 1.390(6) ?
C7 H7 . 0.9500 ?
C8 H8 . 0.9500 ?
C9 C14 . 1.396(6) ?
C9 C10 . 1.398(6) ?
C10 C11 . 1.387(7) ?
C10 H10 . 0.9500 ?
C11 C12 . 1.368(7) ?
C11 H11 . 0.9500 ?
C12 C13 . 1.381(7) ?
C12 H12 . 0.9500 ?
C13 C14 . 1.371(6) ?
C13 H13 . 0.9500 ?
C14 H14 . 0.9500 ?
C21 C21 3_565 1.188(9) yes
C21 C22 . 1.439(6) ?
C22 C23 . 1.393(6) ?
C22 C27 . 1.397(6) ?
C23 C24 . 1.377(7) ?
C23 H23 . 0.9500 ?
C24 C25 . 1.396(7) ?
C24 H24 . 0.9500 ?
C25 C26 . 1.362(8) ?
C25 H25 . 0.9500 ?
C26 C27 . 1.382(7) ?
C26 H26 . 0.9500 ?
C27 H27 . 0.9500 ?
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
_geom_torsion_publ_flag
C4 C3 C1 C2 144.5(5) yes
C3 C1 C2 C9 -4.2(7) yes
C1 C2 C9 C10 -68.6(6) yes
C4 C3 C1 Br1 -37.2(5) yes
C10 C9 C2 Br2 111.1(4) yes
C14 C9 C2 C1 112.5(5) yes
Br1 C1 C2 Br2 -2.0(5) yes
