#------------------------------------------------------------------------------
#$Date: 2016-03-23 03:28:27 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179247 $
#$URL: svn://www.crystallography.net/cod/cif/4/31/67/4316754.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_4316754
loop_
_publ_author_name
'Andreas Orthaber'
'Christiane Seidel'
'Ferdinand Belaj'
'Jörg H. Albering'
'Rudolf Pietschnig'
'Uwe Ruschewitz'
_publ_contact_author_address
; Institute of Chemistry,
  Karl-Franzens University Graz,
  Schubertstr. 1,
  A-8010 Graz,
  Austria
;
_publ_contact_author_email       ferdinand.belaj@uni-graz.at
_publ_contact_author_fax         43(316)3809835
_publ_contact_author_name        'Ferdinand Belaj'
_publ_contact_author_phone       43(316)3805288
_publ_section_title
;
 Optimized Synthesis of Tetrafluoroterephthalic Acid: A Versatile Linking
 Ligand for the Construction of New Coordination Polymers and
 Metal-Organic Frameworks
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              9350
_journal_page_last               9357
_journal_paper_doi               10.1021/ic1009829
_journal_volume                  49
_journal_year                    2010
_chemical_absolute_configuration unk
_chemical_compound_source        'synthetical product'
_chemical_formula_moiety         'C7 H2 F4 O2'
_chemical_formula_sum            'C7 H2 F4 O2'
_chemical_formula_weight         194.09
_chemical_name_systematic        ' 2,3,5,6-Tetrafluoro-benzoic acid'
_space_group_IT_number           43
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'F 2 -2d'
_symmetry_space_group_name_H-M   'F d d 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'manual edited SHELXL-97 .cif file'
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            16
_cell_length_a                   10.1937(15)
_cell_length_b                   12.890(3)
_cell_length_c                   20.425(4)
_cell_measurement_reflns_used    56
_cell_measurement_temperature    95(2)
_cell_measurement_theta_max      17.84
_cell_measurement_theta_min      5.11
_cell_volume                     2683.8(9)
_computing_cell_refinement       'local software'
_computing_data_collection       'local software'
_computing_data_reduction        'local software'
_computing_molecular_graphics    'ORTEP (Johnson, 1965)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      95(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  Stoe
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0162
_diffrn_reflns_av_sigmaI/netI    0.0360
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -1
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -1
_diffrn_reflns_number            898
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.74
_diffrn_standards_decay_%        0.0
_diffrn_standards_interval_count 100
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.210
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.921
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1536
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.178
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    refU
_refine_ls_matrix_type           full
_refine_ls_number_parameters     127
_refine_ls_number_reflns         683
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0275
_refine_ls_R_factor_gt           0.0254
_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/[σ²(Fo²)+(0.0307P)²+0.2967P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0609
_refine_ls_wR_factor_ref         0.0627
_reflns_number_gt                652
_reflns_number_total             683
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic1009829_si_001_4.cif
_cod_data_source_block           ao2
_cod_database_code               4316754
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'-x+1/4, y+1/4, z+1/4'
'x+1/4, -y+1/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'-x+1/4, y+3/4, z+3/4'
'x+1/4, -y+3/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'-x+3/4, y+1/4, z+3/4'
'x+3/4, -y+1/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'-x+3/4, y+3/4, z+1/4'
'x+3/4, -y+3/4, z+1/4'
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
C11 C 0.5000 0.5000 0.95419(16) 0.0176(8) Uani 1 2 d S . .
C12 C 0.4835(2) 0.5914(2) 0.99020(13) 0.0204(6) Uani 1 1 d . . .
C13 C 0.4837(2) 0.59053(19) 1.05757(12) 0.0218(6) Uani 1 1 d . . .
C14 C 0.5000 0.5000 1.09258(19) 0.0243(9) Uani 1 2 d S . .
H14 H 0.5000 0.5000 1.1391 0.035(13) Uiso 1 2 calc SR . .
F12 F 0.46567(14) 0.68283(11) 0.96000(7) 0.0243(4) Uani 1 1 d . . .
F13 F 0.46775(16) 0.68126(12) 1.08930(8) 0.0290(4) Uani 1 1 d . . .
C15 C 0.5000 0.5000 0.88078(17) 0.0187(7) Uani 1 2 d S . .
O15 O 0.5278(2) 0.58408(14) 0.85194(8) 0.0244(5) Uani 1 1 d . . .
H15 H 0.5346 0.5720 0.8062 0.029(16) Uiso 0.50 1 calc PR . .
C21 C 0.5000 0.5000 0.62055(17) 0.0190(8) Uani 1 2 d S . .
C22 C 0.5927(2) 0.55613(19) 0.58516(12) 0.0198(5) Uani 1 1 d . . .
C23 C 0.5928(2) 0.55529(19) 0.51744(12) 0.0225(6) Uani 1 1 d . . .
C24 C 0.5000 0.5000 0.48324(19) 0.0262(9) Uani 1 2 d S . .
H24 H 0.5000 0.5000 0.4367 0.019(10) Uiso 1 2 calc SR . .
F22 F 0.68855(15) 0.60776(12) 0.61594(7) 0.0261(4) Uani 1 1 d . . .
F23 F 0.68549(17) 0.60989(13) 0.48587(8) 0.0321(4) Uani 1 1 d . . .
C25 C 0.5000 0.5000 0.69343(17) 0.0184(7) Uani 1 2 d S . .
O25 O 0.52277(18) 0.58520(14) 0.72251(8) 0.0242(5) Uani 1 1 d . . .
H25 H 0.4980 0.5795 0.7672 0.021(15) Uiso 0.50 1 calc PR . .
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'
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
_geom_angle_publ_flag
C12 C11 C12 116.5(3) . 2_665 ?
C12 C11 C15 121.73(14) . . ?
F12 C12 C13 117.8(2) . . ?
F12 C12 C11 120.9(2) . . ?
C13 C12 C11 121.3(3) . . ?
F13 C13 C12 118.3(2) . . ?
F13 C13 C14 120.0(2) . . ?
C12 C13 C14 121.7(3) . . ?
C13 C14 C13 117.5(3) 2_665 . ?
C13 C14 H14 121.2 . . ?
O15 C15 O15 124.5(3) 2_665 . ?
O15 C15 C11 117.74(16) . . ?
C15 O15 H15 109.5 . . ?
C22 C21 C22 117.5(3) 2_665 . ?
C22 C21 C25 121.27(15) . . ?
F22 C22 C23 118.2(2) . . ?
F22 C22 C21 120.6(2) . . ?
C23 C22 C21 121.0(2) . . ?
F23 C23 C24 120.8(2) . . ?
F23 C23 C22 118.5(2) . . ?
C24 C23 C22 120.8(2) . . ?
C23 C24 C23 118.9(3) . 2_665 ?
C23 C24 H24 120.5 . . ?
O25 C25 O25 124.2(3) . 2_665 ?
O25 C25 C21 117.89(15) . . ?
C25 O25 H25 109.5 . . ?
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
C11 C12 1.399(3) . ?
C11 C15 1.499(5) . ?
C12 F12 1.343(3) . ?
C12 C13 1.376(4) . ?
C13 F13 1.347(3) . ?
C13 C14 1.379(3) . ?
C14 H14 0.95 . ?
C15 O15 1.266(2) . ?
O15 H15 0.95 . ?
C21 C22 1.392(3) . ?
C21 C25 1.488(5) . ?
C22 F22 1.339(3) . ?
C22 C23 1.383(3) . ?
C23 F23 1.343(3) . ?
C23 C24 1.375(3) . ?
C24 H24 0.95 . ?
C25 O25 1.270(2) . ?
O25 H25 0.95 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O15 H15 O25 0.95 1.72 2.644(2) 162.8 .
O25 H25 O15 0.95 1.76 2.644(2) 153.8 .
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
C12 C11 C12 F12 -179.3(3) 2_665 . . . ?
C15 C11 C12 F12 0.7(3) . . . . ?
C12 C11 C12 C13 -0.01(18) 2_665 . . . ?
C15 C11 C12 C13 179.99(18) . . . . ?
F12 C12 C13 F13 -0.9(4) . . . . ?
C11 C12 C13 F13 179.78(17) . . . . ?
F12 C12 C13 C14 179.35(16) . . . . ?
C11 C12 C13 C14 0.0(4) . . . . ?
F13 C13 C14 C13 -179.8(3) . . . 2_665 ?
C12 C13 C14 C13 -0.01(19) . . . 2_665 ?
C12 C11 C15 O15 -157.23(16) . . . 2_665 ?
C12 C11 C15 O15 22.77(16) . . . . ?
C22 C21 C22 F22 -176.7(3) 2_665 . . . ?
C25 C21 C22 F22 3.3(3) . . . . ?
C22 C21 C22 C23 -0.45(18) 2_665 . . . ?
C25 C21 C22 C23 179.55(18) . . . . ?
F22 C22 C23 F23 -2.9(4) . . . . ?
C21 C22 C23 F23 -179.23(17) . . . . ?
F22 C22 C23 C24 177.29(17) . . . . ?
C21 C22 C23 C24 0.9(4) . . . . ?
F23 C23 C24 C23 179.7(2) . . . 2_665 ?
C22 C23 C24 C23 -0.45(18) . . . 2_665 ?
C22 C21 C25 O25 40.63(16) . . . . ?
C22 C21 C25 O25 -139.37(16) . . . 2_665 ?
