#------------------------------------------------------------------------------
#$Date: 2016-03-26 22:02:07 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180488 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/57/7215737.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_7215737
loop_
_publ_author_name
'Wang, Lei'
'Hu, Yanjing'
'Wang, Wenqiang'
'Liu, Faqian'
'Huang, Keke'
_publ_section_title
;
 Energetic multi-component molecular solids of tetrafluoroterephthalic
 acid with some aza compounds by strong hydrogen bonds and weak
 intermolecular interactions of C--H⋯F and C--H⋯O
;
_journal_issue                   20
_journal_name_full               CrystEngComm
_journal_page_first              4142
_journal_paper_doi               10.1039/c4ce00133h
_journal_volume                  16
_journal_year                    2014
_chemical_formula_moiety         'C13 H9 F4 N2 O4'
_chemical_formula_sum            'C13 H9 F4 N2 O4'
_chemical_formula_weight         333.22
_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                94.022(6)
_cell_angle_beta                 109.536(7)
_cell_angle_gamma                90.479(6)
_cell_formula_units_Z            2
_cell_length_a                   7.3027(6)
_cell_length_b                   9.6227(7)
_cell_length_c                   9.7417(7)
_cell_measurement_temperature    293(2)
_cell_volume                     643.20(9)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 'ACTA 50'
_diffrn_measured_fraction_theta_max 0.844
_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  0.0165
_diffrn_reflns_av_sigmaI/netI    0.0358
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4750
_diffrn_reflns_theta_full        'ACTA 50'
_diffrn_reflns_theta_max         29.28
_diffrn_reflns_theta_min         2.22
_exptl_absorpt_coefficient_mu    0.165
_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    1.721
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             338
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.223
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         2956
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0635
_refine_ls_R_factor_gt           0.0448
_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)+(0.0452P)²+0.2137P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1011
_refine_ls_wR_factor_ref         0.1181
_reflns_number_gt                2222
_reflns_number_total             2956
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ce00133h2.cif
_cod_data_source_block           compound6
_cod_original_cell_volume        643.20(8)
_cod_original_sg_symbol_H-M      p-1
_cod_database_code               7215737
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
F1 F 0.40138(18) 0.23164(12) 0.64770(12) 0.0432(3) Uani 1 1 d
F3 F 0.02019(18) -0.07494(12) 0.14349(12) 0.0462(3) Uani 1 1 d
F4 F 0.06340(18) 0.19581(12) 0.13900(12) 0.0453(3) Uani 1 1 d
F2 F 0.3482(2) -0.03726(12) 0.65413(12) 0.0519(4) Uani 1 1 d
O1 O 0.2830(2) -0.28731(14) 0.48459(17) 0.0460(4) Uani 1 1 d
O4 O 0.2279(2) 0.45554(14) 0.48375(16) 0.0462(4) Uani 1 1 d
H4 H 0.2466 0.5378 0.4740 0.080 Uiso 1 1 calc
C6 C 0.1803(3) -0.06800(18) 0.39950(19) 0.0274(4) Uani 1 1 d
C2 C 0.3027(3) 0.15923(18) 0.52115(19) 0.0284(4) Uani 1 1 d
C3 C 0.2346(2) 0.22434(18) 0.39287(19) 0.0267(4) Uani 1 1 d
C5 C 0.1115(3) -0.00168(18) 0.27104(19) 0.0284(4) Uani 1 1 d
C1 C 0.2771(3) 0.01704(19) 0.52374(19) 0.0302(4) Uani 1 1 d
C4 C 0.1382(3) 0.13972(19) 0.26796(18) 0.0284(4) Uani 1 1 d
O3 O 0.3150(2) 0.41854(15) 0.28607(17) 0.0486(4) Uani 1 1 d
C8 C 0.2654(3) 0.37846(19) 0.3827(2) 0.0310(4) Uani 1 1 d
C7 C 0.1455(3) -0.22421(19) 0.4012(2) 0.0326(4) Uani 1 1 d
O2 O -0.0133(2) -0.27330(15) 0.32187(19) 0.0549(5) Uani 1 1 d
N2 N 0.3891(2) 0.68144(16) 0.93643(17) 0.0319(4) Uani 1 1 d
N1 N 0.2010(2) 0.51078(17) 0.8143(2) 0.0415(4) Uani 1 1 d
H1 H 0.1341 0.4538 0.7427 0.080 Uiso 1 1 calc
C12 C 0.5252(3) 0.8030(2) 0.9714(3) 0.0410(5) Uani 1 1 d
H12A H 0.5798 0.8088 0.8937 0.080 Uiso 1 1 calc
H12B H 0.6313 0.7899 1.0608 0.080 Uiso 1 1 calc
C13 C 0.4299(3) 0.9376(2) 0.9898(2) 0.0344(4) Uani 1 1 d
H13A H 0.3876 0.9363 1.0740 0.080 Uiso 1 1 calc
H13B H 0.3161 0.9469 0.9043 0.080 Uiso 1 1 calc
C11 C 0.3090(3) 0.6180(2) 0.8042(2) 0.0388(5) Uani 1 1 d
H11 H 0.3258 0.6443 0.7191 0.080 Uiso 1 1 calc
C9 C 0.3296(3) 0.6121(2) 1.0333(2) 0.0379(5) Uani 1 1 d
H9 H 0.3638 0.6349 1.1333 0.080 Uiso 1 1 calc
C10 C 0.2127(3) 0.5053(2) 0.9564(3) 0.0415(5) Uani 1 1 d
H10 H 0.1511 0.4396 0.9931 0.080 Uiso 1 1 calc
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
C8 O4 H4 109.5 . .
C1 C6 C5 115.68(15) . .
C1 C6 C7 123.14(16) . .
C5 C6 C7 121.16(16) . .
F1 C2 C3 120.90(15) . .
F1 C2 C1 117.60(15) . .
C3 C2 C1 121.48(16) . .
C2 C3 C4 116.31(15) . .
C2 C3 C8 123.70(16) . .
C4 C3 C8 119.95(15) . .
F3 C5 C4 117.46(15) . .
F3 C5 C6 120.58(15) . .
C4 C5 C6 121.93(16) . .
F2 C1 C2 117.26(15) . .
F2 C1 C6 120.23(15) . .
C2 C1 C6 122.50(16) . .
F4 C4 C5 117.96(15) . .
F4 C4 C3 119.94(15) . .
C5 C4 C3 122.09(16) . .
O3 C8 O4 126.47(18) . .
O3 C8 C3 120.58(18) . .
O4 C8 C3 112.92(16) . .
O2 C7 O1 127.64(17) . .
O2 C7 C6 116.53(17) . .
O1 C7 C6 115.83(16) . .
C11 N2 C9 108.67(16) . .
C11 N2 C12 124.62(17) . .
C9 N2 C12 126.66(17) . .
C11 N1 C10 108.96(17) . .
C11 N1 H1 125.5 . .
C10 N1 H1 125.5 . .
N2 C12 C13 112.68(16) . .
N2 C12 H12A 109.1 . .
C13 C12 H12A 109.1 . .
N2 C12 H12B 109.1 . .
C13 C12 H12B 109.1 . .
H12A C12 H12B 107.8 . .
C12 C13 C13 111.1(2) . 2_677
C12 C13 H13A 109.4 . .
C13 C13 H13A 109.4 2_677 .
C12 C13 H13B 109.4 . .
C13 C13 H13B 109.4 2_677 .
H13A C13 H13B 108.0 . .
N1 C11 N2 108.21(18) . .
N1 C11 H11 125.9 . .
N2 C11 H11 125.9 . .
C10 C9 N2 106.88(18) . .
C10 C9 H9 126.6 . .
N2 C9 H9 126.6 . .
C9 C10 N1 107.28(17) . .
C9 C10 H10 126.4 . .
N1 C10 H10 126.4 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
F1 C2 1.3421(19) .
F3 C5 1.3418(19) .
F4 C4 1.3450(19) .
F2 C1 1.346(2) .
O1 C7 1.253(2) .
O4 C8 1.294(2) .
O4 H4 0.8200 .
C6 C1 1.383(2) .
C6 C5 1.387(2) .
C6 C7 1.525(2) .
C2 C3 1.379(2) .
C2 C1 1.383(2) .
C3 C4 1.385(2) .
C3 C8 1.513(2) .
C5 C4 1.377(3) .
O3 C8 1.201(2) .
C7 O2 1.227(2) .
N2 C11 1.324(2) .
N2 C9 1.372(3) .
N2 C12 1.473(2) .
N1 C11 1.322(3) .
N1 C10 1.363(3) .
N1 H1 0.8600 .
C12 C13 1.503(3) .
C12 H12A 0.9700 .
C12 H12B 0.9700 .
C13 C13 1.529(3) 2_677
C13 H13A 0.9700 .
C13 H13B 0.9700 .
C11 H11 0.9300 .
C9 C10 1.340(3) .
C9 H9 0.9300 .
C10 H10 0.9300 .
