#------------------------------------------------------------------------------
#$Date: 2023-03-09 12:31:21 +0200 (Thu, 09 Mar 2023) $
#$Revision: 281774 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/69/8106901.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_8106901
loop_
_publ_author_name
'Chen, Wei'
'Ji, Mian'
'Yang, Shiyong'
_publ_section_title
;
 Crystal structure of bis(2-fluoro-4-nitrophenyl) terephthalate
 C20H10F2N2O8
;
_journal_issue                   2
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              439
_journal_page_last               440
_journal_paper_doi               10.1515/ncrs-2015-0122
_journal_volume                  231
_journal_year                    2016
_chemical_formula_moiety         'C20 H10 F2 N2 O8'
_chemical_formula_sum            'C20 H10 F2 N2 O8'
_chemical_formula_weight         444.30
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_update_record
;
2015-03-24 # Formatted by publCIF
;
_cell_angle_alpha                109.115(11)
_cell_angle_beta                 97.058(11)
_cell_angle_gamma                108.767(11)
_cell_formula_units_Z            2
_cell_length_a                   9.0557(19)
_cell_length_b                   9.2766(17)
_cell_length_c                   12.641(3)
_cell_measurement_reflns_used    2895
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4806
_cell_measurement_theta_min      1.7633
_cell_volume                     918.6(4)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2013)'
_computing_structure_solution
;
'SHELXS (Sheldrick, 2013)'
;
_diffrn_ambient_temperature      173.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device
;
Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_device_details
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'Saturn724+ CCD'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.0330
_diffrn_orient_matrix_UB_12      -0.1127
_diffrn_orient_matrix_UB_13      -0.0277
_diffrn_orient_matrix_UB_21      0.0960
_diffrn_orient_matrix_UB_22      0.0166
_diffrn_orient_matrix_UB_23      -0.0703
_diffrn_orient_matrix_UB_31      0.0265
_diffrn_orient_matrix_UB_32      -0.0044
_diffrn_orient_matrix_UB_33      0.0823
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0325
_diffrn_reflns_av_unetI/netI     0.0288
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10700
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.488
_diffrn_reflns_theta_min         1.763
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           30.0000
_diffrn_source_power             1.5000
_diffrn_source_voltage           50.0000
_exptl_absorpt_coefficient_mu    0.139
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8578
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.606
_exptl_crystal_description       block
_exptl_crystal_F_000             452
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.837
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.134
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         4154
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.134
_refine_ls_R_factor_all          0.0582
_refine_ls_R_factor_gt           0.0537
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0651P)²+0.4106P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1381
_refine_ls_wR_factor_ref         0.1416
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3903
_reflns_number_total             4154
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2015-0122_suppl.cif
_cod_data_source_block           a
_cod_original_cell_volume        918.6(3)
_cod_database_code               8106901
_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.
;
_diffrn_number_total             4155
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C6(H6), C9(H9), C10(H10), C12(H12), C13(H13), C16(H16),
 C17(H17), C19(H19)
;
loop_
_space_group_symop_operation_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_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
F1 F -0.0049(2) 0.4315(2) 0.57291(14) 0.0679(5) Uani 1 1 d . . . . .
F2 F 0.14626(14) 0.64940(17) -0.10640(10) 0.0464(3) Uani 1 1 d . . . . .
O1 O -0.07302(19) 0.2082(2) 0.87305(13) 0.0547(4) Uani 1 1 d . . . . .
O2 O 0.0575(2) 0.04534(18) 0.84671(12) 0.0531(4) Uani 1 1 d . . . . .
O3 O 0.16409(16) 0.28873(15) 0.44380(10) 0.0340(3) Uani 1 1 d . . . . .
O4 O 0.35115(16) 0.53988(16) 0.56000(10) 0.0342(3) Uani 1 1 d . . . . .
O5 O 0.29760(16) 0.44689(16) -0.04461(10) 0.0341(3) Uani 1 1 d . . . . .
O6 O 0.40346(15) 0.71973(15) 0.06830(10) 0.0294(3) Uani 1 1 d . . . . .
O7 O 0.6314(2) 0.9288(2) -0.32625(13) 0.0529(4) Uani 1 1 d . . . . .
O8 O 0.3839(2) 0.9071(2) -0.36450(13) 0.0504(4) Uani 1 1 d . . . . .
N1 N 0.0085(2) 0.1422(2) 0.82103(13) 0.0406(4) Uani 1 1 d . . . . .
N2 N 0.4981(2) 0.8992(2) -0.30696(14) 0.0390(4) Uani 1 1 d . . . . .
C1 C 0.0529(2) 0.1806(2) 0.72228(14) 0.0314(4) Uani 1 1 d . . . . .
C2 C 0.1457(2) 0.1097(2) 0.66331(16) 0.0338(4) Uani 1 1 d . . . . .
H2 H 0.1808 0.0372 0.6850 0.041 Uiso 1 1 calc R . . . .
C3 C 0.1865(2) 0.1481(2) 0.57049(15) 0.0316(4) Uani 1 1 d . . . . .
H3 H 0.2485 0.1009 0.5288 0.038 Uiso 1 1 calc R . . . .
C4 C 0.1340(2) 0.2566(2) 0.54109(14) 0.0298(4) Uani 1 1 d . . . . .
C5 C 0.0420(3) 0.3254(3) 0.60291(17) 0.0383(4) Uani 1 1 d . . . . .
C6 C -0.0017(2) 0.2887(3) 0.69432(17) 0.0386(4) Uani 1 1 d . . . . .
H6 H -0.0650 0.3348 0.7351 0.046 Uiso 1 1 calc R . . . .
C7 C 0.27391(19) 0.4432(2) 0.46482(14) 0.0256(3) Uani 1 1 d . . . . .
C8 C 0.28361(19) 0.4707(2) 0.35598(14) 0.0241(3) Uani 1 1 d . . . . .
C9 C 0.1906(2) 0.3501(2) 0.24830(14) 0.0279(3) Uani 1 1 d . . . . .
H9 H 0.1176 0.2493 0.2427 0.033 Uiso 1 1 calc R . . . .
C10 C 0.2070(2) 0.3804(2) 0.14937(14) 0.0278(3) Uani 1 1 d . . . . .
H10 H 0.1460 0.2992 0.0771 0.033 Uiso 1 1 calc R . . . .
C11 C 0.31465(19) 0.5324(2) 0.15808(14) 0.0246(3) Uani 1 1 d . . . . .
C12 C 0.4040(2) 0.6554(2) 0.26639(15) 0.0302(4) Uani 1 1 d . . . . .
H12 H 0.4733 0.7581 0.2723 0.036 Uiso 1 1 calc R . . . .
C13 C 0.3892(2) 0.6241(2) 0.36529(15) 0.0306(4) Uani 1 1 d . . . . .
H13 H 0.4495 0.7054 0.4377 0.037 Uiso 1 1 calc R . . . .
C14 C 0.33397(19) 0.5556(2) 0.04889(14) 0.0262(3) Uani 1 1 d . . . . .
C15 C 0.4261(2) 0.7572(2) -0.02807(14) 0.0272(3) Uani 1 1 d . . . . .
C16 C 0.5811(2) 0.8388(2) -0.03222(15) 0.0302(4) Uani 1 1 d . . . . .
H16 H 0.6688 0.8623 0.0263 0.036 Uiso 1 1 calc R . . . .
C17 C 0.6051(2) 0.8857(2) -0.12459(16) 0.0319(4) Uani 1 1 d . . . . .
H17 H 0.7087 0.9399 -0.1292 0.038 Uiso 1 1 calc R . . . .
C18 C 0.4724(2) 0.8500(2) -0.20898(15) 0.0312(4) Uani 1 1 d . . . . .
C19 C 0.3159(2) 0.7708(2) -0.20610(15) 0.0330(4) Uani 1 1 d . . . . .
H19 H 0.2282 0.7495 -0.2639 0.040 Uiso 1 1 calc R . . . .
C20 C 0.2952(2) 0.7248(2) -0.11423(15) 0.0309(4) 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'
F F 0.0171 0.0103 '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'
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
C7 O3 C4 116.12(13) . .
C14 O6 C15 116.66(12) . .
O1 N1 O2 123.94(16) . .
O1 N1 C1 118.69(17) . .
O2 N1 C1 117.36(18) . .
O7 N2 O8 124.08(16) . .
O7 N2 C18 118.12(17) . .
O8 N2 C18 117.80(17) . .
C2 C1 N1 119.85(17) . .
C6 C1 N1 117.08(17) . .
C6 C1 C2 123.07(16) . .
C1 C2 C3 118.85(17) . .
C4 C3 C2 119.20(17) . .
C3 C4 O3 120.29(16) . .
C5 C4 O3 119.58(16) . .
C5 C4 C3 119.98(16) . .
F1 C5 C4 118.32(16) . .
F1 C5 C6 119.45(18) . .
C4 C5 C6 122.22(17) . .
C1 C6 C5 116.67(18) . .
O3 C7 C8 111.69(14) . .
O4 C7 O3 122.48(14) . .
O4 C7 C8 125.84(15) . .
C9 C8 C7 122.07(14) . .
C9 C8 C13 120.37(15) . .
C13 C8 C7 117.56(15) . .
C10 C9 C8 119.82(15) . .
C9 C10 C11 119.99(15) . .
C10 C11 C12 120.15(14) . .
C10 C11 C14 117.86(14) . .
C12 C11 C14 121.96(14) . .
C13 C12 C11 119.80(15) . .
C12 C13 C8 119.81(15) . .
O5 C14 O6 123.12(14) . .
O5 C14 C11 125.50(15) . .
O6 C14 C11 111.35(13) . .
C16 C15 O6 118.85(15) . .
C16 C15 C20 120.25(15) . .
C20 C15 O6 120.71(15) . .
C15 C16 C17 119.53(17) . .
C18 C17 C16 118.54(16) . .
C17 C18 N2 118.47(16) . .
C17 C18 C19 123.17(16) . .
C19 C18 N2 118.35(17) . .
C20 C19 C18 117.22(17) . .
F2 C20 C15 118.96(15) . .
F2 C20 C19 119.76(16) . .
C19 C20 C15 121.27(16) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
F1 C5 1.329(2) .
F2 C20 1.338(2) .
O1 N1 1.225(3) .
O2 N1 1.234(2) .
O3 C4 1.3948(19) .
O3 C7 1.372(2) .
O4 C7 1.193(2) .
O5 C14 1.197(2) .
O6 C14 1.369(2) .
O6 C15 1.3927(18) .
O7 N2 1.223(2) .
O8 N2 1.226(2) .
N1 C1 1.473(2) .
N2 C18 1.473(2) .
C1 C2 1.373(3) .
C1 C6 1.372(3) .
C2 C3 1.391(2) .
C3 C4 1.374(3) .
C4 C5 1.373(3) .
C5 C6 1.375(2) .
C7 C8 1.487(2) .
C8 C9 1.389(2) .
C8 C13 1.393(2) .
C9 C10 1.383(2) .
C10 C11 1.393(2) .
C11 C12 1.393(2) .
C11 C14 1.487(2) .
C12 C13 1.385(2) .
C15 C16 1.381(2) .
C15 C20 1.386(3) .
C16 C17 1.391(2) .
C17 C18 1.375(3) .
C18 C19 1.382(3) .
C19 C20 1.376(2) .
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
F1 C5 C6 C1 -178.9(2) . . . .
O1 N1 C1 C2 179.27(17) . . . .
O1 N1 C1 C6 -0.3(2) . . . .
O2 N1 C1 C2 -0.2(2) . . . .
O2 N1 C1 C6 -179.86(17) . . . .
O3 C4 C5 F1 -5.2(3) . . . .
O3 C4 C5 C6 175.10(18) . . . .
O3 C7 C8 C9 -0.3(2) . . . .
O3 C7 C8 C13 179.00(15) . . . .
O4 C7 C8 C9 179.04(17) . . . .
O4 C7 C8 C13 -1.6(3) . . . .
O6 C15 C16 C17 -176.25(14) . . . .
O6 C15 C20 F2 -3.3(2) . . . .
O6 C15 C20 C19 175.79(15) . . . .
O7 N2 C18 C17 18.9(2) . . . .
O7 N2 C18 C19 -161.35(17) . . . .
O8 N2 C18 C17 -161.43(17) . . . .
O8 N2 C18 C19 18.3(2) . . . .
N1 C1 C2 C3 -179.84(15) . . . .
N1 C1 C6 C5 179.21(17) . . . .
N2 C18 C19 C20 179.42(15) . . . .
C1 C2 C3 C4 0.5(3) . . . .
C2 C1 C6 C5 -0.4(3) . . . .
C2 C3 C4 O3 -175.75(15) . . . .
C2 C3 C4 C5 -0.2(3) . . . .
C3 C4 C5 F1 179.18(18) . . . .
C3 C4 C5 C6 -0.5(3) . . . .
C4 O3 C7 O4 6.9(2) . . . .
C4 O3 C7 C8 -173.74(14) . . . .
C4 C5 C6 C1 0.8(3) . . . .
C6 C1 C2 C3 -0.2(3) . . . .
C7 O3 C4 C3 -109.89(19) . . . .
C7 O3 C4 C5 74.5(2) . . . .
C7 C8 C9 C10 -178.45(15) . . . .
C7 C8 C13 C12 179.30(16) . . . .
C8 C9 C10 C11 -1.0(2) . . . .
C9 C8 C13 C12 -1.4(3) . . . .
C9 C10 C11 C12 -1.2(3) . . . .
C9 C10 C11 C14 176.86(15) . . . .
C10 C11 C12 C13 2.0(3) . . . .
C10 C11 C14 O5 -19.3(3) . . . .
C10 C11 C14 O6 162.10(14) . . . .
C11 C12 C13 C8 -0.8(3) . . . .
C12 C11 C14 O5 158.63(18) . . . .
C12 C11 C14 O6 -19.9(2) . . . .
C13 C8 C9 C10 2.3(3) . . . .
C14 O6 C15 C16 -118.24(17) . . . .
C14 O6 C15 C20 66.7(2) . . . .
C14 C11 C12 C13 -175.90(16) . . . .
C15 O6 C14 O5 2.1(2) . . . .
C15 O6 C14 C11 -179.27(13) . . . .
C15 C16 C17 C18 0.5(2) . . . .
C16 C15 C20 F2 -178.26(16) . . . .
C16 C15 C20 C19 0.8(3) . . . .
C16 C17 C18 N2 -179.79(15) . . . .
C16 C17 C18 C19 0.5(3) . . . .
C17 C18 C19 C20 -0.9(3) . . . .
C18 C19 C20 F2 179.27(16) . . . .
C18 C19 C20 C15 0.2(3) . . . .
C20 C15 C16 C17 -1.2(3) . . . .
