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#$Date: 2025-08-22 00:26:11 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301853 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/10/38/7103894.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_7103894
loop_
_publ_author_name
'He, Feng'
'Cheng, Gang'
'Zhang, Haiquan'
'Zheng, Yan'
'Xie, Zengqi'
'Yang, Bing'
'Ma, Yuguang'
'Liu, Shiyong'
'Shen, Jiacong'
_publ_section_title
;
 Synthesis, characteristics and luminescence properties of
 oligo(phenylenevinylene) dimers with a biphenyl linkage center
;
_journal_coden_ASTM              CHCOFS
_journal_issue                   17
_journal_name_full
;
 Chemical Communications (Cambridge, United Kingdom)
;
_journal_page_first              2206
_journal_page_last               2207
_journal_paper_doi               10.1039/b306694k
_journal_year                    2003
_chemical_formula_sum            'C16 H14 Br4'
_chemical_formula_weight         525.91
_chemical_name_common            2,5,2',5'-tetrakis-bromomethyl-biphenyl
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                108.581(11)
_cell_angle_beta                 93.720(6)
_cell_angle_gamma                109.933(15)
_cell_formula_units_Z            2
_cell_length_a                   9.184(2)
_cell_length_b                   9.3868(15)
_cell_length_c                   11.5616(8)
_cell_measurement_reflns_used    6083
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.40
_cell_volume                     871.2(3)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       PROCESS-AUTO
_computing_data_reduction        PROCESS-AUTO
_computing_molecular_graphics    'SHELXL-97 (Sheldrick, 1997)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 10.0
_diffrn_measured_fraction_theta_full 0.900
_diffrn_measured_fraction_theta_max 0.900
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       oscillation
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoKa
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0540
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            3584
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.40
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  .
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    9.227
_exptl_absorpt_correction_T_max  0.2801
_exptl_absorpt_correction_T_min  0.1052
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    2.005
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             500
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.19
_refine_diff_density_max         1.092
_refine_diff_density_min         -0.750
_refine_diff_density_rms         0.148
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     189
_refine_ls_number_reflns         3584
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.1100
_refine_ls_R_factor_gt           0.0646
_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/[s²(Fo²)+(0.1120P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1786
_refine_ls_wR_factor_ref         0.1980
_reflns_number_gt                2084
_reflns_number_total             3584
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b306694k.txt
_cod_data_source_block           ma02-01
_cod_original_sg_symbol_H-M      p-1
_cod_database_code               7103894
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.27953(12) 0.75924(11) 0.33258(7) 0.0666(3) Uani 1 1 d . . .
Br2 Br 0.17721(14) 0.75450(12) 1.02489(8) 0.0727(3) Uani 1 1 d . . .
Br3 Br 0.20174(13) 1.20711(11) 0.58530(7) 0.0671(3) Uani 1 1 d . . .
Br4 Br 0.32975(15) 1.28446(14) 1.30377(8) 0.0826(4) Uani 1 1 d . . .
C1 C 0.3909(11) 0.7505(10) 0.4806(6) 0.054(2) Uani 1 1 d . . .
H1A H 0.4093 0.6502 0.4578 0.065 Uiso 1 1 calc R . .
H1B H 0.4926 0.8406 0.5109 0.065 Uiso 1 1 calc R . .
C2 C 0.0565(10) 0.7751(10) 0.8877(7) 0.058(2) Uani 1 1 d . . .
H2A H -0.0459 0.6859 0.8588 0.070 Uiso 1 1 calc R . .
H2B H 0.0391 0.8758 0.9183 0.070 Uiso 1 1 calc R . .
C3 C 0.0917(10) 1.1243(9) 0.7067(6) 0.0508(19) Uani 1 1 d . . .
H3A H 0.0050 1.1605 0.7201 0.061 Uiso 1 1 calc R . .
H3B H 0.0478 1.0063 0.6725 0.061 Uiso 1 1 calc R . .
C4 C 0.4721(11) 1.3514(11) 1.1934(7) 0.070(3) Uani 1 1 d . . .
H4A H 0.5238 1.4690 1.2246 0.084 Uiso 1 1 calc R . .
H4B H 0.5529 1.3064 1.1922 0.084 Uiso 1 1 calc R . .
C11 C 0.2955(9) 0.7591(8) 0.5823(6) 0.0434(17) Uani 1 1 d . . .
C12 C 0.1962(10) 0.6168(9) 0.5937(7) 0.0514(19) Uani 1 1 d . . .
H12A H 0.1814 0.5158 0.5354 0.062 Uiso 1 1 calc R . .
C13 C 0.1196(10) 0.6285(9) 0.6936(7) 0.053(2) Uani 1 1 d . . .
H13A H 0.0518 0.5331 0.7003 0.064 Uiso 1 1 calc R . .
C14 C 0.1389(9) 0.7740(8) 0.7831(6) 0.0437(17) Uani 1 1 d . . .
C15 C 0.2378(8) 0.9158(8) 0.7694(6) 0.0385(15) Uani 1 1 d . . .
C16 C 0.3153(9) 0.9061(8) 0.6704(6) 0.0433(17) Uani 1 1 d . . .
H16A H 0.3824 1.0014 0.6633 0.052 Uiso 1 1 calc R . .
C21 C 0.1975(9) 1.1802(8) 0.8259(6) 0.0426(17) Uani 1 1 d . . .
C22 C 0.2612(9) 1.0810(8) 0.8595(6) 0.0398(15) Uani 1 1 d . . .
C23 C 0.3520(9) 1.1368(9) 0.9776(6) 0.0452(18) Uani 1 1 d . . .
H23 H 0.374(9) 1.077(8) 1.009(6) 0.037(19) Uiso 1 1 d . . .
C24 C 0.3794(9) 1.2922(9) 1.0642(6) 0.0472(18) Uani 1 1 d . . .
C25 C 0.3175(10) 1.3905(9) 1.0287(6) 0.0504(19) Uani 1 1 d . . .
H25A H 0.3365 1.4945 1.0842 0.061 Uiso 1 1 calc R . .
C26 C 0.2281(11) 1.3353(10) 0.9120(7) 0.0512(19) Uani 1 1 d . . .
H26 H 0.180(9) 1.398(8) 0.884(6) 0.038(18) Uiso 1 1 d . . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 C1 Br1 110.9(6) . . ?
C14 C2 Br2 111.9(6) . . ?
C21 C3 Br3 112.1(6) . . ?
C24 C4 Br4 109.8(6) . . ?
C16 C11 C12 119.1(7) . . ?
C16 C11 C1 120.7(7) . . ?
C12 C11 C1 119.9(7) . . ?
C13 C12 C11 118.7(7) . . ?
C14 C13 C12 123.1(7) . . ?
C13 C14 C15 117.5(7) . . ?
C13 C14 C2 119.5(7) . . ?
C15 C14 C2 123.0(7) . . ?
C16 C15 C14 120.1(6) . . ?
C16 C15 C22 118.4(6) . . ?
C14 C15 C22 121.5(6) . . ?
C11 C16 C15 121.6(7) . . ?
C22 C21 C26 118.8(6) . . ?
C22 C21 C3 122.3(6) . . ?
C26 C21 C3 118.8(7) . . ?
C23 C22 C21 119.8(6) . . ?
C23 C22 C15 119.0(7) . . ?
C21 C22 C15 121.3(6) . . ?
C22 C23 C24 120.8(7) . . ?
C25 C24 C23 118.7(7) . . ?
C25 C24 C4 119.9(7) . . ?
C23 C24 C4 121.4(8) . . ?
C26 C25 C24 120.3(7) . . ?
C25 C26 C21 121.6(7) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C1 1.975(7) . ?
Br2 C2 1.975(9) . ?
Br3 C3 1.985(8) . ?
Br4 C4 1.975(9) . ?
C1 C11 1.510(10) . ?
C2 C14 1.467(10) . ?
C3 C21 1.461(10) . ?
C4 C24 1.499(10) . ?
C11 C16 1.373(10) . ?
C11 C12 1.389(10) . ?
C12 C13 1.385(11) . ?
C13 C14 1.370(11) . ?
C14 C15 1.397(10) . ?
C15 C16 1.381(10) . ?
C15 C22 1.500(9) . ?
C21 C22 1.390(10) . ?
C21 C26 1.396(10) . ?
C22 C23 1.390(9) . ?
C23 C24 1.407(10) . ?
C24 C25 1.383(11) . ?
C25 C26 1.373(11) . ?
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br1 C1 C11 C16 -90.9(8) . . . . ?
Br1 C1 C11 C12 94.6(7) . . . . ?
C16 C11 C12 C13 0.4(11) . . . . ?
C1 C11 C12 C13 175.0(7) . . . . ?
C11 C12 C13 C14 -1.0(13) . . . . ?
C12 C13 C14 C15 1.7(12) . . . . ?
C12 C13 C14 C2 -178.4(8) . . . . ?
Br2 C2 C14 C13 86.1(8) . . . . ?
Br2 C2 C14 C15 -94.0(8) . . . . ?
C13 C14 C15 C16 -1.8(11) . . . . ?
C2 C14 C15 C16 178.3(7) . . . . ?
C13 C14 C15 C22 177.4(7) . . . . ?
C2 C14 C15 C22 -2.5(11) . . . . ?
C12 C11 C16 C15 -0.6(11) . . . . ?
C1 C11 C16 C15 -175.1(7) . . . . ?
C14 C15 C16 C11 1.3(11) . . . . ?
C22 C15 C16 C11 -178.0(7) . . . . ?
Br3 C3 C21 C22 -101.9(7) . . . . ?
Br3 C3 C21 C26 82.1(8) . . . . ?
C26 C21 C22 C23 0.6(11) . . . . ?
C3 C21 C22 C23 -175.4(7) . . . . ?
C26 C21 C22 C15 -177.6(7) . . . . ?
C3 C21 C22 C15 6.4(11) . . . . ?
C16 C15 C22 C23 -107.5(8) . . . . ?
C14 C15 C22 C23 73.2(10) . . . . ?
C16 C15 C22 C21 70.7(10) . . . . ?
C14 C15 C22 C21 -108.6(8) . . . . ?
C21 C22 C23 C24 0.5(12) . . . . ?
C15 C22 C23 C24 178.8(7) . . . . ?
C22 C23 C24 C25 -1.5(12) . . . . ?
C22 C23 C24 C4 177.7(8) . . . . ?
Br4 C4 C24 C25 91.4(8) . . . . ?
Br4 C4 C24 C23 -87.9(9) . . . . ?
C23 C24 C25 C26 1.4(12) . . . . ?
C4 C24 C25 C26 -177.8(8) . . . . ?
C24 C25 C26 C21 -0.3(13) . . . . ?
C22 C21 C26 C25 -0.7(12) . . . . ?
C3 C21 C26 C25 175.4(8) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 4418097
2 PubChem 5251158
