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#$Date: 2025-08-22 23:12:46 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301866 $
#$URL: svn://www.crystallography.net/cod/cif/7/23/47/7234768.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_7234768
loop_
_publ_author_name
'Fangyi Chen'
'Taiji Tian'
'Binglian Bai'
'Jian Wang'
'Haitao Wang'
'Min Li'
_publ_section_title
;
 Crystal structures, intermolecular interactions and fluorescence
 properties of a series of symmetrical bi-1,3,4-oxadiazole derivatives
;
_journal_name_full               'Journal of Materials Chemistry C'
_journal_page_first              4451
_journal_page_last               4458
_journal_paper_doi               10.1039/C6TC00324A
_journal_volume                  4
_journal_year                    2016
_chemical_formula_sum            'C16 H8 F2 N4 O2'
_chemical_formula_weight         326.26
_chemical_name_common            BOXD-o-F
_chemical_name_systematic        2,2-bis(2-fluorophenyl)-bi-1,3,4-oxadiazole
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 95.88(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.0707(16)
_cell_length_b                   6.1870(12)
_cell_length_c                   13.704(3)
_cell_measurement_reflns_used    1538
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.46
_cell_measurement_theta_min      3.62
_cell_volume                     680.7(2)
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_collection       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_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  0.0539
_diffrn_reflns_av_sigmaI/netI    0.0554
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6219
_diffrn_reflns_theta_full        27.46
_diffrn_reflns_theta_max         27.46
_diffrn_reflns_theta_min         3.62
_exptl_absorpt_coefficient_mu    0.128
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.592
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             332
_refine_diff_density_max         0.412
_refine_diff_density_min         -0.360
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     109
_refine_ls_number_reflns         1538
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.089
_refine_ls_R_factor_all          0.0853
_refine_ls_R_factor_gt           0.0577
_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)+(0.0974P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1578
_refine_ls_wR_factor_ref         0.1770
_reflns_number_gt                1039
_reflns_number_total             1538
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            J-Mater-Chem-C-2016-4-4451.cif
_cod_data_source_block           boxd-o-f
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7234768
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.10002(18) 0.2061(2) 1.01864(10) 0.0550(5) Uani 1 1 d . . .
O1 O 0.42018(18) -0.2690(2) 0.92934(11) 0.0390(5) Uani 1 1 d . . .
C7 C 0.3127(3) -0.1228(4) 0.96378(16) 0.0380(5) Uani 1 1 d . . .
C4 C 0.2559(3) 0.0551(4) 0.89871(16) 0.0384(5) Uani 1 1 d . . .
N1 N 0.2789(2) -0.1698(3) 1.05138(14) 0.0481(6) Uani 1 1 d . . .
C3 C 0.3078(3) 0.0720(4) 0.80537(16) 0.0440(6) Uani 1 1 d . . .
H3 H 0.3779 -0.0330 0.7836 0.053 Uiso 1 1 calc R . .
C5 C 0.1503(3) 0.2153(4) 0.92839(17) 0.0394(6) Uani 1 1 d . . .
C8 C 0.4442(3) -0.4081(3) 1.00518(16) 0.0386(5) Uani 1 1 d . . .
C1 C 0.1513(3) 0.3984(4) 0.77605(18) 0.0488(6) Uani 1 1 d . . .
H1 H 0.1166 0.5130 0.7350 0.059 Uiso 1 1 calc R . .
C2 C 0.2567(3) 0.2425(4) 0.74444(18) 0.0489(6) Uani 1 1 d . . .
H2 H 0.2931 0.2525 0.6824 0.059 Uiso 1 1 calc R . .
N2 N 0.3660(3) -0.3601(3) 1.07840(15) 0.0476(6) Uani 1 1 d . . .
C6 C 0.0972(3) 0.3846(4) 0.86831(18) 0.0470(6) Uani 1 1 d . . .
H6 H 0.0258 0.4887 0.8895 0.056 Uiso 1 1 calc R . .
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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C8 O1 C7 101.65(17) . .
N1 C7 O1 111.9(2) . .
N1 C7 C4 130.8(2) . .
O1 C7 C4 117.21(19) . .
C3 C4 C5 117.8(2) . .
C3 C4 C7 120.9(2) . .
C5 C4 C7 121.4(2) . .
C7 N1 N2 106.64(18) . .
C2 C3 C4 120.9(2) . .
F1 C5 C6 118.7(2) . .
F1 C5 C4 119.4(2) . .
C6 C5 C4 122.0(2) . .
N2 C8 O1 114.49(19) . .
N2 C8 C8 128.0(3) . 3_647
O1 C8 C8 117.5(2) . 3_647
C6 C1 C2 120.3(2) . .
C3 C2 C1 119.8(2) . .
C8 N2 N1 105.27(17) . .
C5 C6 C1 119.2(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
F1 C5 1.342(3) .
O1 C8 1.348(3) .
O1 C7 1.370(3) .
C7 N1 1.291(3) .
C7 C4 1.461(3) .
C4 C3 1.390(3) .
C4 C5 1.395(3) .
N1 N2 1.402(3) .
C3 C2 1.382(3) .
C5 C6 1.373(3) .
C8 N2 1.274(3) .
C8 C8 1.466(4) 3_647
C1 C6 1.382(3) .
C1 C2 1.385(3) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 13680552
