#------------------------------------------------------------------------------
#$Date: 2016-03-23 02:28:27 +0100 (Wed, 23 Mar 2016) $
#$Revision: 179247 $
#$URL: svn://saulius.grazulis.lt/cod-secondary/cif/4/31/67/4316753.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_4316753
loop_
_publ_author_name
'Andreas Orthaber'
'Christiane Seidel'
'Ferdinand Belaj'
'J\"org 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_formula_moiety         'C8 F4 O4, 2(H4 N)'
_chemical_formula_sum            'C8 H8 F4 N2 O4'
_chemical_formula_weight         272.16
_chemical_name_common            Diammonium-2,3,5,6-tetrafluoroterephthalate
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           12
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2y'
_symmetry_space_group_name_H-M   'C 1 2/m 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 92.38(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   6.632(2)
_cell_length_b                   19.771(6)
_cell_length_c                   3.7145(11)
_cell_measurement_reflns_used    701
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      59.53
_cell_measurement_theta_min      2.29
_cell_volume                     486.6(3)
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2001)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Altomare, 1993)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Stoe IPDS II'
_diffrn_measurement_method       '\f 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  0.0536
_diffrn_reflns_av_sigmaI/netI    0.0397
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       4
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            2857
_diffrn_reflns_theta_full        29.53
_diffrn_reflns_theta_max         29.53
_diffrn_reflns_theta_min         2.06
_diffrn_standards_decay_%        none
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.194
_exptl_absorpt_correction_T_max  0.9110
_exptl_absorpt_correction_T_min  0.7558
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
(X-RED; Stoe & Cie, 2001; the crystal shape was optimized by
X-SHAPE; Stoe & Cie, 1999)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.857
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plates
_exptl_crystal_F_000             276
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.264
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       0.023(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     52
_refine_ls_number_reflns         701
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.001
_refine_ls_R_factor_all          0.0640
_refine_ls_R_factor_gt           0.0413
_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/[\s^2^(Fo^2^)+(0.0514P)^2^+0.1764P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0942
_refine_ls_wR_factor_ref         0.1030
_reflns_number_gt                479
_reflns_number_total             701
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic1009829_si_001_3.cif
_cod_data_source_block           cs065
_cod_original_sg_symbol_H-M      'C 2/m'
_cod_database_code               4316753
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 1.33109(14) 0.06670(5) 0.7612(3) 0.0446(4) Uani 1 1 d . . .
O1 O 0.84697(19) 0.17799(6) 0.6085(4) 0.0431(4) Uani 1 1 d . . .
N1 N 1.5000 0.20413(10) 1.0000 0.0370(5) Uani 1 2 d SD . .
C1 C 1.0000 0.07218(9) 0.5000 0.0266(5) Uani 1 2 d S . .
C2 C 1.0000 0.14929(10) 0.5000 0.0300(5) Uani 1 2 d S . .
C3 C 1.1661(2) 0.03490(7) 0.6251(4) 0.0286(4) Uani 1 1 d . . .
H1 H 1.395(3) 0.1796(12) 1.121(7) 0.067(7) Uiso 1 1 d D . .
H2 H 1.437(4) 0.2351(11) 0.823(6) 0.076(8) Uiso 1 1 d D . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
F1 0.0318(6) 0.0338(5) 0.0666(8) -0.0044(5) -0.0155(5) -0.0066(4)
O1 0.0400(7) 0.0292(6) 0.0612(9) -0.0053(5) 0.0144(6) 0.0040(5)
N1 0.0335(10) 0.0329(10) 0.0448(12) 0.000 0.0052(9) 0.000
C1 0.0267(10) 0.0239(9) 0.0294(10) 0.000 0.0030(8) 0.000
C2 0.0311(11) 0.0235(9) 0.0356(11) 0.000 0.0029(8) 0.000
C3 0.0246(7) 0.0269(7) 0.0341(8) -0.0022(6) -0.0024(6) -0.0029(5)
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
_geom_angle_publ_flag
H1 N1 H2 109(2) . . ?
C3 C1 C3 115.91(17) 2_756 . ?
C3 C1 C2 122.05(9) 2_756 . ?
C3 C1 C2 122.05(9) . . ?
O1 C2 O1 125.7(2) . 2_756 ?
O1 C2 C1 117.13(10) . . ?
O1 C2 C1 117.13(10) 2_756 . ?
F1 C3 C3 117.93(7) . 6 ?
F1 C3 C1 120.00(13) . . ?
C3 C3 C1 122.05(9) 6 . ?
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
F1 C3 1.3425(16) . ?
O1 C2 1.2444(15) . ?
N1 H1 0.973(16) . ?
N1 H2 0.978(16) . ?
C1 C3 1.3893(17) 2_756 ?
C1 C3 1.3893(17) . ?
C1 C2 1.524(3) . ?
C2 O1 1.2444(15) 2_756 ?
C3 C3 1.380(3) 6 ?
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
N1 H1 O1 0.973(16) 1.929(19) 2.8205(16) 151(2) 2_757
N1 H2 O1 0.978(16) 1.977(18) 2.908(2) 158(2) 8
