#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/58/2215810.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2215810
loop_
_publ_author_name
'Wang, Shou-Xin '
'Tian, Lai-Jin'
_publ_section_title
;
 4,5,6,7-Tetrafluoro-2-(2-hydroxyphenyl)isoindoline-1,3-dione
;
_journal_coeditor_code           BT2541
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o4382
_journal_page_last               o4382
_journal_paper_doi               10.1107/S1600536807050908
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C14 H5 F4 N O3'
_chemical_formula_moiety         'C14 H5 F4 N O3'
_chemical_formula_sum            'C14 H5 F4 N O3'
_chemical_formula_weight         311.19
_chemical_name_systematic
;
4,5,6,7-Tetrafluoro-2-(2-hydroxyphenyl)isoindoline-1,3-dione
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.1741(14)
_cell_length_b                   8.5862(17)
_cell_length_c                   19.994(4)
_cell_measurement_reflns_used    5027
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      27.88
_cell_measurement_theta_min      2.58
_cell_volume                     1231.6(4)
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_collection       'SMART (Bruker, 2002)'
_computing_data_reduction        'SAINT (Bruker, 2002)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'SHELXL97 (Bruker, 2002)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.0218
_diffrn_reflns_av_sigmaI/netI    0.0130
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            9661
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.04
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.158
_exptl_absorpt_correction_T_max  0.9701
_exptl_absorpt_correction_T_min  0.9452
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2002)'
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.678
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.151
_refine_diff_density_min         -0.164
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         1421
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.085
_refine_ls_R_factor_all          0.0304
_refine_ls_R_factor_gt           0.0290
_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)+(0.0461P)²+0.1954P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0768
_refine_ls_wR_factor_ref         0.0783
_reflns_number_gt                1357
_reflns_number_total             1421
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt2541.cif
_cod_data_source_block           I
_cod_database_code               2215810
_cod_database_fobs_code          2215810
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
O O2 -0.1913(2) 0.8342(2) 1.01130(8) 0.0506(4) Uani d . 1
C C1 0.2077(3) 0.9716(2) 0.93266(10) 0.0323(4) Uani d . 1
O O1 0.30879(19) 0.9848(2) 0.88482(7) 0.0418(4) Uani d . 1
C C2 0.2369(3) 1.0283(2) 1.00242(10) 0.0331(4) Uani d . 1
C C3 0.3795(3) 1.1116(3) 1.02994(11) 0.0376(5) Uani d . 1
C C4 0.3656(3) 1.1581(3) 1.09631(12) 0.0433(5) Uani d . 1
C C5 0.2105(4) 1.1218(3) 1.13324(11) 0.0456(5) Uani d . 1
C C6 0.0671(3) 1.0354(3) 1.10543(11) 0.0436(5) Uani d . 1
C C7 0.0816(3) 0.9886(2) 1.04006(10) 0.0361(4) Uani d . 1
C C8 -0.0482(3) 0.8983(2) 0.99679(10) 0.0362(4) Uani d . 1
C C9 -0.0515(3) 0.8314(3) 0.87496(10) 0.0347(4) Uani d . 1
C C10 0.0392(3) 0.7145(3) 0.84035(11) 0.0465(5) Uani d . 1
H H10 0.1556 0.6800 0.8544 0.056 Uiso calc R 1
C C11 -0.0441(4) 0.6494(3) 0.78494(12) 0.0581(7) Uani d . 1
H H11 0.0171 0.5718 0.7610 0.070 Uiso calc R 1
C C12 -0.2181(4) 0.6990(3) 0.76485(12) 0.0573(7) Uani d . 1
H H12 -0.2748 0.6536 0.7278 0.069 Uiso calc R 1
C C13 -0.3084(4) 0.8156(3) 0.79935(11) 0.0504(6) Uani d . 1
H H13 -0.4260 0.8482 0.7857 0.061 Uiso calc R 1
C C14 -0.2247(3) 0.8843(3) 0.85420(10) 0.0370(5) Uani d . 1
F F1 0.53099(17) 1.15288(17) 0.99578(7) 0.0536(4) Uani d . 1
F F2 0.5037(2) 1.23938(19) 1.12395(8) 0.0605(4) Uani d . 1
F F3 0.1976(3) 1.17079(19) 1.19626(7) 0.0649(4) Uani d . 1
F F4 -0.0821(2) 1.0039(2) 1.14282(7) 0.0665(5) Uani d . 1
N N1 0.0331(2) 0.9009(2) 0.93265(8) 0.0327(4) Uani d . 1
O O3 -0.3012(2) 1.0052(2) 0.88828(9) 0.0508(4) Uani d . 1
H H3 -0.4151 1.0014 0.8851 0.076 Uiso calc R 1
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
O1 C1 N1 125.62(19)
O1 C1 C2 128.77(18)
N1 C1 C2 105.60(16)
C3 C2 C7 120.82(19)
C3 C2 C1 130.82(19)
C7 C2 C1 108.30(17)
F1 C3 C2 123.0(2)
F1 C3 C4 118.1(2)
C2 C3 C4 118.8(2)
F2 C4 C5 119.9(2)
F2 C4 C3 119.6(2)
C5 C4 C3 120.5(2)
F3 C5 C4 119.6(2)
F3 C5 C6 119.8(2)
C4 C5 C6 120.5(2)
F4 C6 C7 122.4(2)
F4 C6 C5 118.7(2)
C7 C6 C5 118.9(2)
C6 C7 C2 120.4(2)
C6 C7 C8 131.2(2)
C2 C7 C8 108.38(18)
O2 C8 N1 125.6(2)
O2 C8 C7 129.3(2)
N1 C8 C7 105.14(16)
C10 C9 C14 120.6(2)
C10 C9 N1 120.38(19)
C14 C9 N1 118.98(19)
C11 C10 C9 119.6(2)
C11 C10 H10 120.2
C9 C10 H10 120.2
C10 C11 C12 120.1(3)
C10 C11 H11 120.0
C12 C11 H11 120.0
C13 C12 C11 120.3(2)
C13 C12 H12 119.9
C11 C12 H12 119.9
C12 C13 C14 120.2(2)
C12 C13 H13 119.9
C14 C13 H13 119.9
O3 C14 C13 123.3(2)
O3 C14 C9 117.53(19)
C13 C14 C9 119.2(2)
C1 N1 C8 112.31(16)
C1 N1 C9 124.25(16)
C8 N1 C9 123.37(17)
C14 O3 H3 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O2 C8 1.200(3)
C1 O1 1.206(2)
C1 N1 1.391(3)
C1 C2 1.492(3)
C2 C3 1.364(3)
C2 C7 1.387(3)
C3 F1 1.332(2)
C3 C4 1.389(3)
C4 F2 1.332(2)
C4 C5 1.371(3)
C5 F3 1.332(3)
C5 C6 1.385(3)
C6 F4 1.333(3)
C6 C7 1.371(3)
C7 C8 1.489(3)
C8 N1 1.409(3)
C9 C10 1.382(3)
C9 C14 1.386(3)
C9 N1 1.434(3)
C10 C11 1.377(3)
C10 H10 0.9300
C11 C12 1.379(4)
C11 H11 0.9300
C12 C13 1.377(4)
C12 H12 0.9300
C13 C14 1.382(3)
C13 H13 0.9300
C14 O3 1.358(3)
O3 H3 0.8200
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O3 H3 O1 1_455 0.82 1.99 2.804(2) 175.3
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
O1 C1 C2 C3 1.8(4)
N1 C1 C2 C3 -176.8(2)
O1 C1 C2 C7 179.0(2)
N1 C1 C2 C7 0.4(2)
C7 C2 C3 F1 -179.78(19)
C1 C2 C3 F1 -3.0(4)
C7 C2 C3 C4 -0.9(3)
C1 C2 C3 C4 175.9(2)
F1 C3 C4 F2 -1.1(3)
C2 C3 C4 F2 180.0(2)
F1 C3 C4 C5 178.5(2)
C2 C3 C4 C5 -0.5(3)
F2 C4 C5 F3 1.3(4)
C3 C4 C5 F3 -178.3(2)
F2 C4 C5 C6 -179.0(2)
C3 C4 C5 C6 1.4(4)
F3 C5 C6 F4 0.3(4)
C4 C5 C6 F4 -179.3(2)
F3 C5 C6 C7 178.8(2)
C4 C5 C6 C7 -0.9(4)
F4 C6 C7 C2 177.9(2)
C5 C6 C7 C2 -0.5(3)
F4 C6 C7 C8 -0.6(4)
C5 C6 C7 C8 -179.0(2)
C3 C2 C7 C6 1.4(3)
C1 C2 C7 C6 -176.1(2)
C3 C2 C7 C8 -179.76(19)
C1 C2 C7 C8 2.8(2)
C6 C7 C8 O2 -6.8(4)
C2 C7 C8 O2 174.6(2)
C6 C7 C8 N1 173.8(2)
C2 C7 C8 N1 -4.8(2)
C14 C9 C10 C11 -0.4(3)
N1 C9 C10 C11 -179.8(2)
C9 C10 C11 C12 -1.0(4)
C10 C11 C12 C13 1.1(4)
C11 C12 C13 C14 0.3(4)
C12 C13 C14 O3 176.4(2)
C12 C13 C14 C9 -1.7(3)
C10 C9 C14 O3 -176.4(2)
N1 C9 C14 O3 3.0(3)
C10 C9 C14 C13 1.7(3)
N1 C9 C14 C13 -178.8(2)
O1 C1 N1 C8 177.7(2)
C2 C1 N1 C8 -3.6(2)
O1 C1 N1 C9 0.6(3)
C2 C1 N1 C9 179.30(18)
O2 C8 N1 C1 -174.2(2)
C7 C8 N1 C1 5.2(2)
O2 C8 N1 C9 2.9(3)
C7 C8 N1 C9 -177.65(18)
C10 C9 N1 C1 56.7(3)
C14 C9 N1 C1 -122.8(2)
C10 C9 N1 C8 -120.0(2)
C14 C9 N1 C8 60.5(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21121347
