#------------------------------------------------------------------------------
#$Date: 2016-03-26 18:23:59 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180427 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/96/7209655.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_7209655
loop_
_publ_author_name
'Wang, Lei'
'Zhao, Lei'
'Hu, Yanjing'
'Wang, Wenqiang'
'Chen, Ruixin'
'Yang, Yu'
_publ_section_title
;
 A cooperation molecular recognition study: syntheses and analysis of
 supramolecular assemblies of tetrafluoroterephthalic acid with some aza
 compounds
;
_journal_issue                   15
_journal_name_full               CrystEngComm
_journal_page_first              2835
_journal_paper_doi               10.1039/c3ce26865a
_journal_volume                  15
_journal_year                    2013
_chemical_formula_moiety         'C20 H12 F4 N2 O5'
_chemical_formula_sum            'C20 H12 F4 N2 O5'
_chemical_formula_weight         436.32
_chemical_melting_point          ?
_chemical_name_systematic
;
?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                79.34(3)
_cell_angle_beta                 81.08(3)
_cell_angle_gamma                66.64(3)
_cell_formula_units_Z            2
_cell_length_a                   7.8627(16)
_cell_length_b                   9.6759(19)
_cell_length_c                   13.503(3)
_cell_measurement_temperature    293(2)
_cell_volume                     923.0(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    SHELXP-97
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 12.00cm
_diffrn_measured_fraction_theta_full 0.969
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0199
_diffrn_reflns_av_sigmaI/netI    0.0263
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            8923
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.01
_diffrn_standards_decay_%        none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_number         none
_exptl_absorpt_coefficient_mu    0.140
_exptl_absorpt_correction_T_max  0.0001
_exptl_absorpt_correction_T_min  0.0001
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.570
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             444
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.536
_refine_diff_density_min         -0.457
_refine_diff_density_rms         0.088
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     288
_refine_ls_number_reflns         4101
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0699
_refine_ls_R_factor_gt           0.0475
_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)+(0.1234P)²+0.1010P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1461
_refine_ls_wR_factor_ref         0.1883
_reflns_number_gt                2897
_reflns_number_total             4101
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3ce26865a.txt
_cod_data_source_block           w134
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value 'not measured' was changed to '?' -
the value is undefined or not given.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_cell_volume        923.0(3)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7209655
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
F1 F 0.18788(17) 0.40080(12) 0.01381(9) 0.0458(3) Uani 1 1 d .
F2 F -0.09694(19) 0.33354(13) 0.34555(9) 0.0529(4) Uani 1 1 d .
F3 F 0.2527(2) 0.11906(13) -0.00396(10) 0.0554(4) Uani 1 1 d .
F4 F -0.0293(2) 0.05057(14) 0.32642(11) 0.0613(4) Uani 1 1 d .
O1 O -0.1666(2) 0.61470(15) 0.23116(13) 0.0497(4) Uani 1 1 d .
O3 O 0.3105(2) -0.16848(15) 0.11963(15) 0.0561(5) Uani 1 1 d .
O2 O 0.1041(2) 0.60307(14) 0.14606(15) 0.0569(5) Uani 1 1 d .
H2 H 0.0669 0.6926 0.1543 0.080 Uiso 1 1 calc .
C16 C -0.0128(3) 0.28504(18) 0.25734(14) 0.0335(4) Uani 1 1 d .
C18 C 0.1314(2) 0.31812(17) 0.09335(14) 0.0308(4) Uani 1 1 d .
C17 C 0.0387(2) 0.38073(17) 0.17957(14) 0.0301(4) Uani 1 1 d .
C19 C 0.1658(3) 0.16922(19) 0.08356(14) 0.0340(4) Uani 1 1 d .
O4 O 0.0132(2) -0.12668(16) 0.16575(17) 0.0649(6) Uani 1 1 d .
C14 C 0.1108(2) 0.07496(18) 0.15986(15) 0.0333(4) Uani 1 1 d .
C13 C -0.0154(2) 0.54787(18) 0.18814(14) 0.0332(4) Uani 1 1 d .
C20 C 0.1519(3) -0.08907(19) 0.14713(17) 0.0394(4) Uani 1 1 d .
C15 C 0.0232(3) 0.13579(19) 0.24709(15) 0.0371(4) Uani 1 1 d .
N1 N 0.5317(2) 0.18218(18) 0.21593(13) 0.0400(4) Uani 1 1 d .
C4 C 0.3126(3) 0.3708(2) 0.44111(17) 0.0474(5) Uani 1 1 d .
C5 C 0.3731(3) 0.2595(2) 0.37624(15) 0.0387(4) Uani 1 1 d .
N2 N 0.3462(3) 0.1273(2) 0.39888(15) 0.0492(5) Uani 1 1 d .
H5 H 0.3840 0.0618 0.3571 0.080 Uiso 1 1 calc .
C8 C 0.4672(2) 0.2889(2) 0.27981(15) 0.0354(4) Uani 1 1 d .
C9 C 0.4924(3) 0.4271(2) 0.24913(15) 0.0396(4) Uani 1 1 d .
C11 C 0.6361(3) 0.3416(2) 0.08884(17) 0.0471(5) Uani 1 1 d .
H11A H 0.6906 0.3581 0.0239 0.057 Uiso 1 1 calc R
C10 C 0.5759(3) 0.4521(2) 0.15213(17) 0.0444(5) Uani 1 1 d .
H10A H 0.5911 0.5437 0.1299 0.053 Uiso 1 1 calc R
C7 C 0.4273(3) 0.5373(2) 0.31824(19) 0.0523(6) Uani 1 1 d .
H7A H 0.4442 0.6288 0.2996 0.063 Uiso 1 1 calc R
C12 C 0.6134(3) 0.2060(2) 0.12415(16) 0.0435(5) Uani 1 1 d .
H12A H 0.6563 0.1298 0.0829 0.052 Uiso 1 1 calc R
C1 C 0.2594(4) 0.1036(3) 0.4878(2) 0.0583(6) Uani 1 1 d .
H1A H 0.2386 0.0136 0.5042 0.070 Uiso 1 1 calc R
C2 C 0.1963(4) 0.2047(3) 0.5592(2) 0.0667(7) Uani 1 1 d .
H2A H 0.1381 0.1811 0.6217 0.080 Uiso 1 1 calc R
C3 C 0.2219(4) 0.3385(3) 0.5356(2) 0.0640(7) Uani 1 1 d .
H3A H 0.1797 0.4082 0.5816 0.077 Uiso 1 1 calc R
C6 C 0.3422(4) 0.5098(3) 0.40946(19) 0.0579(6) Uani 1 1 d .
H6A H 0.3015 0.5828 0.4532 0.069 Uiso 1 1 calc R
O1W O 0.5503(3) 0.90092(18) 0.21738(16) 0.0609(5) Uani 1 1 d D
H1WA H 0.654(3) 0.832(4) 0.216(3) 0.130(16) Uiso 1 1 d D
H1WB H 0.487(4) 0.883(4) 0.182(2) 0.091(12) Uiso 1 1 d 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
C13 O2 H2 109.5
F2 C16 C15 117.66(16)
F2 C16 C17 120.95(14)
C15 C16 C17 121.39(17)
F1 C18 C17 121.21(14)
F1 C18 C19 117.03(16)
C17 C18 C19 121.73(16)
C18 C17 C16 116.47(14)
C18 C17 C13 122.45(16)
C16 C17 C13 121.00(16)
F3 C19 C14 120.48(15)
F3 C19 C18 117.63(17)
C14 C19 C18 121.88(17)
C15 C14 C19 116.49(15)
C15 C14 C20 122.81(17)
C19 C14 C20 120.68(17)
O1 C13 O2 127.15(15)
O1 C13 C17 118.16(16)
O2 C13 C17 114.66(15)
O3 C20 O4 126.93(16)
O3 C20 C14 118.40(17)
O4 C20 C14 114.66(16)
F4 C15 C14 120.47(15)
F4 C15 C16 117.52(17)
C14 C15 C16 122.01(17)
C12 N1 C8 121.98(17)
C5 C4 C3 116.7(2)
C5 C4 C6 120.0(2)
C3 C4 C6 123.3(2)
N2 C5 C4 123.88(19)
N2 C5 C8 118.23(18)
C4 C5 C8 117.89(19)
C1 N2 C5 116.8(2)
C1 N2 H5 121.6
C5 N2 H5 121.6
N1 C8 C9 119.07(18)
N1 C8 C5 119.55(18)
C9 C8 C5 121.37(18)
C10 C9 C8 118.55(18)
C10 C9 C7 123.00(19)
C8 C9 C7 118.43(19)
C12 C11 C10 118.6(2)
C12 C11 H11A 120.7
C10 C11 H11A 120.7
C11 C10 C9 120.42(19)
C11 C10 H10A 119.8
C9 C10 H10A 119.8
C6 C7 C9 120.7(2)
C6 C7 H7A 119.7
C9 C7 H7A 119.7
N1 C12 C11 121.37(19)
N1 C12 H12A 119.3
C11 C12 H12A 119.3
N2 C1 C2 124.3(2)
N2 C1 H1A 117.8
C2 C1 H1A 117.8
C3 C2 C1 118.6(2)
C3 C2 H2A 120.7
C1 C2 H2A 120.7
C2 C3 C4 119.7(2)
C2 C3 H3A 120.2
C4 C3 H3A 120.2
C7 C6 C4 121.5(2)
C7 C6 H6A 119.2
C4 C6 H6A 119.2
H1WA O1W H1WB 107(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
F1 C18 1.344(2)
F2 C16 1.339(2)
F3 C19 1.341(2)
F4 C15 1.343(2)
O1 C13 1.218(2)
O3 C20 1.219(2)
O2 C13 1.270(2)
O2 H2 0.8200
C16 C15 1.387(2)
C16 C17 1.389(3)
C18 C17 1.379(2)
C18 C19 1.384(2)
C17 C13 1.523(2)
C19 C14 1.381(3)
O4 C20 1.257(3)
C14 C15 1.375(3)
C14 C20 1.526(2)
N1 C12 1.330(3)
N1 C8 1.359(2)
C4 C5 1.403(3)
C4 C3 1.407(3)
C4 C6 1.432(3)
C5 N2 1.350(3)
C5 C8 1.433(3)
N2 C1 1.315(3)
N2 H5 0.8600
C8 C9 1.407(3)
C9 C10 1.395(3)
C9 C7 1.434(3)
C11 C12 1.381(3)
C11 C10 1.382(3)
C11 H11A 0.9300
C10 H10A 0.9300
C7 C6 1.342(3)
C7 H7A 0.9300
C12 H12A 0.9300
C1 C2 1.396(4)
C1 H1A 0.9300
C2 C3 1.361(4)
C2 H2A 0.9300
C3 H3A 0.9300
C6 H6A 0.9300
O1W H1WA 0.821(18)
O1W H1WB 0.824(17)
