#------------------------------------------------------------------------------
#$Date: 2025-08-22 23:12:46 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301866 $
#$URL: svn://www.crystallography.net/cod/cif/7/23/47/7234770.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_7234770
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-p-F
_chemical_name_systematic        2,2-bis(4-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                 99.63(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.425(3)
_cell_length_b                   3.8641(8)
_cell_length_c                   27.628(6)
_cell_measurement_reflns_used    3188
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      3.08
_cell_volume                     1413.0(5)
_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 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  0.0450
_diffrn_reflns_av_sigmaI/netI    0.0432
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            12410
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.08
_exptl_absorpt_coefficient_mu    0.123
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.534
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             664
_refine_diff_density_max         0.199
_refine_diff_density_min         -0.134
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.926
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3188
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.926
_refine_ls_R_factor_all          0.0932
_refine_ls_R_factor_gt           0.0433
_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)+(0.0557P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0952
_refine_ls_wR_factor_ref         0.1127
_reflns_number_gt                1688
_reflns_number_total             3188
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            J-Mater-Chem-C-2016-4-4451.cif
_cod_data_source_block           boxd-p-f
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               7234770
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
O1 O 0.38372(8) 0.1121(3) 0.45959(4) 0.0458(3) Uani 1 1 d . . .
C7 C 0.36259(13) 0.0043(4) 0.41192(6) 0.0430(4) Uani 1 1 d . . .
C4 C 0.26673(12) 0.1053(4) 0.38276(6) 0.0424(4) Uani 1 1 d . . .
F1 F -0.00536(8) 0.3593(4) 0.30032(5) 0.0887(5) Uani 1 1 d . . .
N1 N 0.43356(11) -0.1860(4) 0.39981(5) 0.0549(4) Uani 1 1 d . . .
O2 O 0.91537(11) 0.0122(3) 0.44155(5) 0.0633(4) Uani 1 1 d . . .
N2 N 0.50912(11) -0.2082(4) 0.44183(6) 0.0536(4) Uani 1 1 d . . .
C8 C 0.47599(12) -0.0304(4) 0.47493(6) 0.0443(4) Uani 1 1 d . . .
C2 C 0.10185(14) 0.3596(5) 0.37629(7) 0.0554(5) Uani 1 1 d . . .
H2 H 0.0527 0.4739 0.3903 0.066 Uiso 1 1 calc R . .
C5 C 0.24692(14) 0.0233(5) 0.33296(6) 0.0523(5) Uani 1 1 d . . .
H5 H 0.2958 -0.0883 0.3184 0.063 Uiso 1 1 calc R . .
C16 C 0.95164(16) 0.0714(5) 0.48984(8) 0.0621(5) Uani 1 1 d . . .
C3 C 0.19396(13) 0.2734(5) 0.40415(7) 0.0479(4) Uani 1 1 d . . .
H3 H 0.2071 0.3286 0.4374 0.057 Uiso 1 1 calc R . .
C12 C 0.76270(16) 0.1866(5) 0.38685(8) 0.0590(5) Uani 1 1 d . . .
C1 C 0.08502(14) 0.2727(5) 0.32784(7) 0.0579(5) Uani 1 1 d . . .
C15 C 0.82410(16) 0.1830(5) 0.43506(8) 0.0609(5) Uani 1 1 d . . .
N4 N 0.89252(15) 0.2556(5) 0.51127(7) 0.0741(5) Uani 1 1 d . . .
N3 N 0.80821(15) 0.3307(5) 0.47521(7) 0.0751(5) Uani 1 1 d . . .
C6 C 0.15472(15) 0.1077(5) 0.30512(7) 0.0587(5) Uani 1 1 d . . .
H6 H 0.1405 0.0538 0.2719 0.070 Uiso 1 1 calc R . .
C13 C 0.66499(17) 0.3255(5) 0.38080(9) 0.0690(6) Uani 1 1 d . . .
H13 H 0.6396 0.4073 0.4080 0.083 Uiso 1 1 calc R . .
F2 F 0.59001(11) 0.2404(4) 0.25022(6) 0.1052(5) Uani 1 1 d . . .
C11 C 0.79948(17) 0.0623(5) 0.34626(8) 0.0665(6) Uani 1 1 d . . .
H11 H 0.8638 -0.0340 0.3500 0.080 Uiso 1 1 calc R . .
C10 C 0.74075(19) 0.0811(6) 0.30012(9) 0.0740(6) Uani 1 1 d . . .
H10 H 0.7653 0.0015 0.2726 0.089 Uiso 1 1 calc R . .
C9 C 0.64593(19) 0.2192(6) 0.29586(9) 0.0740(6) Uani 1 1 d . . .
C14 C 0.60636(18) 0.3421(6) 0.33506(10) 0.0745(6) Uani 1 1 d . . .
H14 H 0.5415 0.4343 0.3309 0.089 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 102.07(14) . .
N1 C7 O1 112.37(15) . .
N1 C7 C4 129.26(16) . .
O1 C7 C4 118.35(16) . .
C3 C4 C5 119.75(16) . .
C3 C4 C7 120.79(16) . .
C5 C4 C7 119.44(17) . .
C7 N1 N2 106.35(14) . .
C16 O2 C15 102.21(16) . .
C8 N2 N1 105.49(14) . .
N2 C8 O1 113.72(14) . .
N2 C8 C8 128.2(2) . 3_656
O1 C8 C8 118.1(2) . 3_656
C1 C2 C3 118.26(19) . .
C6 C5 C4 120.06(19) . .
N4 C16 O2 113.48(19) . .
N4 C16 C16 128.5(3) . 3_756
O2 C16 C16 118.1(2) . 3_756
C2 C3 C4 120.26(17) . .
C11 C12 C13 119.3(2) . .
C11 C12 C15 121.2(2) . .
C13 C12 C15 119.47(19) . .
F1 C1 C2 118.3(2) . .
F1 C1 C6 118.19(18) . .
C2 C1 C6 123.50(17) . .
N3 C15 O2 111.7(2) . .
N3 C15 C12 129.4(2) . .
O2 C15 C12 118.85(17) . .
C16 N4 N3 105.91(18) . .
C15 N3 N4 106.68(18) . .
C1 C6 C5 118.17(18) . .
C14 C13 C12 120.6(2) . .
C10 C11 C12 120.2(2) . .
C9 C10 C11 118.6(2) . .
F2 C9 C10 117.8(2) . .
F2 C9 C14 119.1(2) . .
C10 C9 C14 123.1(2) . .
C9 C14 C13 118.2(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C8 1.3570(19) .
O1 C7 1.365(2) .
C7 N1 1.291(2) .
C7 C4 1.453(2) .
C4 C3 1.385(2) .
C4 C5 1.393(2) .
F1 C1 1.361(2) .
N1 N2 1.411(2) .
O2 C16 1.361(2) .
O2 C15 1.377(2) .
N2 C8 1.281(2) .
C8 C8 1.446(3) 3_656
C2 C1 1.362(3) .
C2 C3 1.383(2) .
C5 C6 1.382(3) .
C16 N4 1.282(3) .
C16 C16 1.436(4) 3_756
C12 C11 1.384(3) .
C12 C13 1.401(3) .
C12 C15 1.445(3) .
C1 C6 1.368(3) .
C15 N3 1.296(3) .
N4 N3 1.407(3) .
C13 C14 1.374(3) .
F2 C9 1.358(3) .
C11 C10 1.384(3) .
C10 C9 1.367(3) .
C9 C14 1.369(3) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168339070
