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#$Date: 2022-06-30 10:22:38 +0300 (Thu, 30 Jun 2022) $
#$Revision: 276427 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/55/8105572.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_8105572
loop_
_publ_author_name
'Zhou, Zhixu'
'Long, Dan'
'Wu, Qing-Mei'
'Yu, De-Hou'
'Lu, Hong-Guang'
_publ_section_title
;
 The crystal structure of 2-(4-fluorophenyl)-1,3,4-oxadiazole, C8H5FN2O
;
_journal_issue                   1
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              153
_journal_page_last               154
_journal_paper_doi               10.1515/ncrs-2018-0242
_journal_volume                  234
_journal_year                    2018
_chemical_formula_sum            'C8 H5 F N2 O'
_chemical_formula_weight         164.14
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90.08(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.892(8)
_cell_length_b                   6.088(6)
_cell_length_c                   15.701(16)
_cell_measurement_reflns_used    1422
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      21.62
_cell_measurement_theta_min      2.58
_cell_volume                     754.4(13)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  CCD
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0363
_diffrn_reflns_av_unetI/netI     0.0441
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            4791
_diffrn_reflns_point_group_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        25.147
_diffrn_reflns_theta_max         25.147
_diffrn_reflns_theta_min         2.581
_exptl_absorpt_coefficient_mu    0.116
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.445
_exptl_crystal_description       Block
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_exptl_transmission_factor_max   0.864
_exptl_transmission_factor_min   0.864
_refine_diff_density_max         0.121
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details
;
 Flack x determined using 719 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(7)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.971
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         2635
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.971
_refine_ls_R_factor_all          0.0569
_refine_ls_R_factor_gt           0.0423
_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)+(0.0540P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0924
_refine_ls_wR_factor_ref         0.1032
_reflns_Friedel_coverage         0.802
_reflns_Friedel_fraction_full    0.962
_reflns_Friedel_fraction_max     0.962
_reflns_number_gt                2048
_reflns_number_total             2635
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2018-0242_suppl.cif
_cod_data_source_block           1
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               8105572
_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.
;
_shelx_estimated_absorpt_t_min   0.975
_shelx_estimated_absorpt_t_max   0.979
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1106(4) 0.4691(7) 0.6429(3) 0.0744(10) Uani 1 1 d . . . . .
C2 C 0.1149(4) 0.5379(6) 0.7264(2) 0.0739(10) Uani 1 1 d . . . . .
H2 H 0.0689 0.6728 0.7419 0.089 Uiso 1 1 calc R U . . .
C3 C 0.1888(4) 0.4029(6) 0.7871(2) 0.0661(9) Uani 1 1 d . . . . .
H3 H 0.1925 0.4464 0.8439 0.079 Uiso 1 1 calc R U . . .
C4 C 0.2576(4) 0.2019(5) 0.7628(2) 0.0560(8) Uani 1 1 d . . . . .
C5 C 0.2508(4) 0.1385(6) 0.6775(2) 0.0693(9) Uani 1 1 d . . . . .
H5 H 0.2972 0.0047 0.6609 0.083 Uiso 1 1 calc R U . . .
C6 C 0.1754(4) 0.2736(7) 0.6170(3) 0.0785(11) Uani 1 1 d . . . . .
H6 H 0.1695 0.2312 0.5601 0.094 Uiso 1 1 calc R U . . .
C7 C 0.3388(4) 0.0599(5) 0.8258(2) 0.0566(8) Uani 1 1 d . . . . .
C8 C 0.4258(5) -0.0442(6) 0.9472(2) 0.0783(10) Uani 1 1 d . . . . .
H8 H 0.4477 -0.0500 1.0053 0.094 Uiso 1 1 calc R U . . .
C9 C 0.3655(4) 0.8908(7) 0.4014(3) 0.0812(11) Uani 1 1 d . . . . .
C10 C 0.2907(4) 0.6886(7) 0.4021(2) 0.0803(11) Uani 1 1 d . . . . .
H10 H 0.2766 0.6112 0.4527 0.096 Uiso 1 1 calc R U . . .
C11 C 0.2361(4) 0.6019(6) 0.3247(2) 0.0663(9) Uani 1 1 d . . . . .
H11 H 0.1853 0.4642 0.3233 0.080 Uiso 1 1 calc R U . . .
C12 C 0.2571(3) 0.7198(6) 0.2496(2) 0.0561(8) Uani 1 1 d . . . . .
C13 C 0.3348(4) 0.9241(5) 0.2519(2) 0.0685(9) Uani 1 1 d . . . . .
H13 H 0.3497 1.0035 0.2019 0.082 Uiso 1 1 calc R U . . .
C14 C 0.3901(4) 1.0095(7) 0.3287(3) 0.0804(11) Uani 1 1 d . . . . .
H14 H 0.4432 1.1457 0.3308 0.096 Uiso 1 1 calc R U . . .
C15 C 0.1985(4) 0.6311(6) 0.1674(2) 0.0600(8) Uani 1 1 d . . . . .
C16 C 0.0946(5) 0.4029(9) 0.0806(3) 0.0905(12) Uani 1 1 d . . . . .
H16 H 0.0469 0.2758 0.0581 0.109 Uiso 1 1 calc R U . . .
F1 F 0.0381(3) 0.6011(4) 0.58288(15) 0.1069(8) Uani 1 1 d . . . . .
F2 F 0.4186(3) 0.9754(5) 0.47792(16) 0.1269(11) Uani 1 1 d . . . . .
N1 N 0.4158(4) -0.1219(5) 0.81395(18) 0.0702(8) Uani 1 1 d . . . . .
N2 N 0.4732(4) -0.1923(5) 0.8952(2) 0.0768(8) Uani 1 1 d . . . . .
N3 N 0.1987(4) 0.7232(6) 0.0931(2) 0.0812(9) Uani 1 1 d . . . . .
N4 N 0.1296(4) 0.5694(7) 0.0357(2) 0.0912(10) Uani 1 1 d . . . . .
O1 O 0.3413(3) 0.1213(4) 0.90992(14) 0.0765(7) Uani 1 1 d . . . . .
O2 O 0.1333(3) 0.4263(4) 0.16505(15) 0.0762(7) Uani 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'
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
C6 C1 F1 117.8(4) . .
C6 C1 C2 122.9(4) . .
F1 C1 C2 119.2(4) . .
C1 C2 C3 118.9(4) . .
C2 C3 C4 119.8(4) . .
C3 C4 C5 119.5(3) . .
C3 C4 C7 120.4(3) . .
C5 C4 C7 120.1(3) . .
C6 C5 C4 120.5(3) . .
C1 C6 C5 118.3(4) . .
N1 C7 O1 111.8(3) . .
N1 C7 C4 128.5(3) . .
O1 C7 C4 119.7(3) . .
N2 C8 O1 113.5(3) . .
C14 C9 C10 123.1(4) . .
C14 C9 F2 119.3(4) . .
C10 C9 F2 117.6(4) . .
C9 C10 C11 117.9(4) . .
C10 C11 C12 120.5(3) . .
C13 C12 C11 119.6(3) . .
C13 C12 C15 119.3(3) . .
C11 C12 C15 121.1(3) . .
C14 C13 C12 119.9(4) . .
C9 C14 C13 119.0(4) . .
N3 C15 O2 112.1(3) . .
N3 C15 C12 129.0(3) . .
O2 C15 C12 118.8(3) . .
N4 C16 O2 114.1(4) . .
C7 N1 N2 106.4(3) . .
C8 N2 N1 105.6(3) . .
C15 N3 N4 106.7(3) . .
C16 N4 N3 105.1(3) . .
C8 O1 C7 102.8(3) . .
C15 O2 C16 102.0(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C6 1.358(6) .
C1 F1 1.364(4) .
C1 C2 1.377(5) .
C2 C3 1.387(5) .
C3 C4 1.392(5) .
C4 C5 1.396(5) .
C4 C7 1.461(5) .
C5 C6 1.390(5) .
C7 N1 1.276(4) .
C7 O1 1.373(4) .
C8 N2 1.272(5) .
C8 O1 1.342(4) .
C9 C14 1.366(6) .
C9 C10 1.365(6) .
C9 F2 1.372(4) .
C10 C11 1.393(5) .
C11 C12 1.391(5) .
C12 C13 1.387(5) .
C12 C15 1.473(5) .
C13 C14 1.383(5) .
C15 N3 1.294(4) .
C15 O2 1.349(4) .
C16 N4 1.265(5) .
C16 O2 1.367(4) .
N1 N2 1.420(4) .
N3 N4 1.409(5) .
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
C6 C1 C2 C3 0.2(5) . . . .
F1 C1 C2 C3 180.0(3) . . . .
C1 C2 C3 C4 0.2(5) . . . .
C2 C3 C4 C5 -0.2(4) . . . .
C2 C3 C4 C7 178.8(3) . . . .
C3 C4 C5 C6 -0.4(4) . . . .
C7 C4 C5 C6 -179.3(3) . . . .
F1 C1 C6 C5 179.5(3) . . . .
C2 C1 C6 C5 -0.7(5) . . . .
C4 C5 C6 C1 0.8(5) . . . .
C3 C4 C7 N1 -175.8(3) . . . .
C5 C4 C7 N1 3.2(5) . . . .
C3 C4 C7 O1 2.6(4) . . . .
C5 C4 C7 O1 -178.5(3) . . . .
C14 C9 C10 C11 -0.6(5) . . . .
F2 C9 C10 C11 179.9(3) . . . .
C9 C10 C11 C12 -0.4(5) . . . .
C10 C11 C12 C13 0.8(4) . . . .
C10 C11 C12 C15 -179.4(3) . . . .
C11 C12 C13 C14 -0.3(4) . . . .
C15 C12 C13 C14 179.9(3) . . . .
C10 C9 C14 C13 1.0(6) . . . .
F2 C9 C14 C13 -179.4(3) . . . .
C12 C13 C14 C9 -0.6(5) . . . .
C13 C12 C15 N3 -4.8(5) . . . .
C11 C12 C15 N3 175.4(3) . . . .
C13 C12 C15 O2 175.7(3) . . . .
C11 C12 C15 O2 -4.1(4) . . . .
O1 C7 N1 N2 0.9(3) . . . .
C4 C7 N1 N2 179.3(3) . . . .
O1 C8 N2 N1 0.1(4) . . . .
C7 N1 N2 C8 -0.6(4) . . . .
O2 C15 N3 N4 -0.5(4) . . . .
C12 C15 N3 N4 180.0(3) . . . .
O2 C16 N4 N3 0.0(5) . . . .
C15 N3 N4 C16 0.3(4) . . . .
N2 C8 O1 C7 0.4(4) . . . .
N1 C7 O1 C8 -0.8(3) . . . .
C4 C7 O1 C8 -179.4(3) . . . .
N3 C15 O2 C16 0.4(3) . . . .
C12 C15 O2 C16 -179.9(3) . . . .
N4 C16 O2 C15 -0.2(4) . . . .
