#------------------------------------------------------------------------------
#$Date: 2016-03-05 12:46:23 +0200 (Sat, 05 Mar 2016) $
#$Revision: 177917 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/49/7154920.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_7154920
loop_
_publ_author_name
'Galán, Elena'
'Perrin, Mickael L.'
'Lutz, Martin'
'van der Zant, Herre S. J.'
'Grozema, Ferdinand C.'
'Eelkema, Rienk'
_publ_section_title
;
 Synthesis of 1,2-biphenylethane based single-molecule diodes.
;
_journal_issue                   8
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              2439
_journal_page_last               2443
_journal_paper_doi               10.1039/c6ob00008h
_journal_volume                  14
_journal_year                    2016
_chemical_formula_moiety         'C14 H10 Br2 F2'
_chemical_formula_sum            'C14 H10 Br2 F2'
_chemical_formula_weight         376.04
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     heavy
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2016-01-04 deposited with the CCDC.
2016-01-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.173(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.0789(5)
_cell_length_b                   5.2425(5)
_cell_length_c                   31.267(2)
_cell_measurement_reflns_used    15233
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      1.96
_cell_volume                     1318.88(17)
_computing_cell_refinement       Peakref
_computing_data_collection       Apex2
_computing_data_reduction        'Eval15, SADABS-2014/4'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    SHELXT
_diffrn_ambient_temperature      110(2)
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_device_type  'Bruker Kappa ApexII'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0533
_diffrn_reflns_av_unetI/netI     0.0298
_diffrn_reflns_laue_measured_fraction_full 0.979
_diffrn_reflns_laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            22039
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.505
_diffrn_reflns_theta_min         2.531
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    6.148
_exptl_absorpt_correction_T_max  0.4305
_exptl_absorpt_correction_T_min  0.2297
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS-2014/4
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.894
_exptl_crystal_description       plate
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.04
_refine_diff_density_max         1.904
_refine_diff_density_min         -1.226
_refine_diff_density_rms         0.181
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.180
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2935
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.180
_refine_ls_R_factor_all          0.0821
_refine_ls_R_factor_gt           0.0675
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0640P)²+15.9912P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1836
_refine_ls_wR_factor_ref         0.1940
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2354
_reflns_number_total             2935
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c6ob00008h2.cif
_cod_data_source_block           l0752a
_cod_depositor_comments          'Adding full bibliography for 7154920.cif.'
_cod_original_cell_volume        1318.90(17)
_cod_database_code               7154920
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
Br1 Br 0.22371(9) 0.07757(18) -0.08249(2) 0.0364(3) Uani 1 1 d . .
Br2 Br 0.27345(12) -0.06832(19) 0.33449(3) 0.0449(3) Uani 1 1 d . .
F1 F 0.1285(6) -0.3866(8) 0.05966(16) 0.0347(10) Uani 1 1 d . .
F2 F 0.4547(5) 0.3554(8) 0.06900(14) 0.0318(10) Uani 1 1 d . .
C1 C 0.2066(9) 0.1279(14) 0.1386(2) 0.0279(15) Uani 1 1 d . .
H1A H 0.2346 0.3081 0.1332 0.033 Uiso 1 1 calc R U
H1B H 0.0900 0.0990 0.1271 0.033 Uiso 1 1 calc R U
C2 C 0.3204(9) -0.0452(13) 0.1154(2) 0.0275(15) Uani 1 1 d . .
H2A H 0.4374 -0.0045 0.1251 0.033 Uiso 1 1 calc R U
H2B H 0.2999 -0.2247 0.1232 0.033 Uiso 1 1 calc R U
C3 C 0.2953(8) -0.0187(13) 0.0673(2) 0.0236(14) Uani 1 1 d . .
C4 C 0.2025(8) -0.1851(13) 0.0405(2) 0.0245(14) Uani 1 1 d . .
C5 C 0.1766(8) -0.1665(14) -0.0033(2) 0.0256(15) Uani 1 1 d . .
H5 H 0.1113 -0.2883 -0.0198 0.031 Uiso 1 1 calc R U
C6 C 0.2491(8) 0.0361(14) -0.0224(2) 0.0239(14) Uani 1 1 d . .
C7 C 0.3443(8) 0.2140(13) 0.0020(2) 0.0237(14) Uani 1 1 d . .
H7 H 0.3951 0.3532 -0.0112 0.028 Uiso 1 1 calc R U
C8 C 0.3624(8) 0.1824(13) 0.0455(2) 0.0238(14) Uani 1 1 d . .
C9 C 0.2228(8) 0.0794(13) 0.1864(2) 0.0251(14) Uani 1 1 d . .
C10 C 0.1445(8) -0.1237(14) 0.2039(2) 0.0276(15) Uani 1 1 d . .
H10 H 0.0789 -0.2359 0.1856 0.033 Uiso 1 1 calc R U
C11 C 0.1594(10) -0.1684(15) 0.2480(3) 0.0315(16) Uani 1 1 d . .
H11 H 0.1040 -0.3086 0.2596 0.038 Uiso 1 1 calc R U
C12 C 0.2557(9) -0.0059(15) 0.2744(2) 0.0284(15) Uani 1 1 d . .
C13 C 0.3346(8) 0.2006(14) 0.2580(2) 0.0269(15) Uani 1 1 d . .
H13 H 0.3987 0.3139 0.2766 0.032 Uiso 1 1 calc R U
C14 C 0.3187(8) 0.2401(13) 0.2141(2) 0.0246(14) Uani 1 1 d . .
H14 H 0.3746 0.3801 0.2025 0.029 Uiso 1 1 calc R U
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'
F F 0.0171 0.0103 '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
C9 C1 C2 111.8(6)
C9 C1 H1A 109.3
C2 C1 H1A 109.3
C9 C1 H1B 109.3
C2 C1 H1B 109.3
H1A C1 H1B 107.9
C3 C2 C1 112.9(6)
C3 C2 H2A 109.0
C1 C2 H2A 109.0
C3 C2 H2B 109.0
C1 C2 H2B 109.0
H2A C2 H2B 107.8
C4 C3 C8 113.2(6)
C4 C3 C2 124.4(6)
C8 C3 C2 122.4(6)
C5 C4 F1 117.2(6)
C5 C4 C3 125.9(6)
F1 C4 C3 116.9(7)
C4 C5 C6 117.1(6)
C4 C5 H5 121.4
C6 C5 H5 121.4
C5 C6 C7 121.0(7)
C5 C6 Br1 120.6(5)
C7 C6 Br1 118.4(5)
C8 C7 C6 118.1(7)
C8 C7 H7 121.0
C6 C7 H7 121.0
F2 C8 C7 117.7(6)
F2 C8 C3 117.6(6)
C7 C8 C3 124.7(6)
C10 C9 C14 118.0(7)
C10 C9 C1 121.5(7)
C14 C9 C1 120.4(7)
C9 C10 C11 121.5(7)
C9 C10 H10 119.2
C11 C10 H10 119.2
C12 C11 C10 118.9(7)
C12 C11 H11 120.5
C10 C11 H11 120.5
C11 C12 C13 121.2(7)
C11 C12 Br2 118.4(6)
C13 C12 Br2 120.4(6)
C12 C13 C14 118.8(7)
C12 C13 H13 120.6
C14 C13 H13 120.6
C13 C14 C9 121.5(6)
C13 C14 H14 119.2
C9 C14 H14 119.2
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C6 1.884(7)
Br2 C12 1.899(7)
F1 C4 1.378(8)
F2 C8 1.350(8)
C1 C9 1.508(10)
C1 C2 1.523(9)
C1 H1A 0.9900
C1 H1B 0.9900
C2 C3 1.504(10)
C2 H2A 0.9900
C2 H2B 0.9900
C3 C4 1.384(10)
C3 C8 1.392(10)
C4 C5 1.370(11)
C5 C6 1.375(10)
C5 H5 0.9500
C6 C7 1.392(10)
C7 C8 1.363(10)
C7 H7 0.9500
C9 C10 1.377(10)
C9 C14 1.392(10)
C10 C11 1.391(11)
C10 H10 0.9500
C11 C12 1.378(11)
C11 H11 0.9500
C12 C13 1.378(11)
C13 C14 1.385(11)
C13 H13 0.9500
C14 H14 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
C9 C1 C2 C3 174.6(6)
C1 C2 C3 C4 -99.8(8)
C1 C2 C3 C8 79.1(8)
C8 C3 C4 C5 0.9(10)
C2 C3 C4 C5 179.8(6)
C8 C3 C4 F1 -178.6(5)
C2 C3 C4 F1 0.4(9)
F1 C4 C5 C6 179.4(5)
C3 C4 C5 C6 -0.1(10)
C4 C5 C6 C7 -0.1(9)
C4 C5 C6 Br1 179.2(5)
C5 C6 C7 C8 -0.5(9)
Br1 C6 C7 C8 -179.9(5)
C6 C7 C8 F2 180.0(5)
C6 C7 C8 C3 1.4(10)
C4 C3 C8 F2 179.9(5)
C2 C3 C8 F2 0.9(9)
C4 C3 C8 C7 -1.6(9)
C2 C3 C8 C7 179.5(6)
C2 C1 C9 C10 -79.4(9)
C2 C1 C9 C14 100.3(8)
C14 C9 C10 C11 0.2(10)
C1 C9 C10 C11 -180.0(7)
C9 C10 C11 C12 -0.4(11)
C10 C11 C12 C13 1.0(11)
C10 C11 C12 Br2 179.6(5)
C11 C12 C13 C14 -1.4(11)
Br2 C12 C13 C14 180.0(5)
C12 C13 C14 C9 1.3(10)
C10 C9 C14 C13 -0.7(10)
C1 C9 C14 C13 179.5(6)
