#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/42/2214259.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_2214259
loop_
_publ_author_name
'Fan Wen'
'Ren-Jie Ni'
'Cheng Yao'
_publ_section_title
;
 Tetrafluoro-N-phenylphthalimide
;
_journal_coeditor_code           HK2269
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3153
_journal_page_last               o3153
_journal_paper_doi               10.1107/S1600536807027286
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C14 H5 F4 N O2'
_chemical_formula_moiety         'C14 H5 F4 N O2'
_chemical_formula_sum            'C14 H5 F4 N O2'
_chemical_formula_weight         295.19
_chemical_name_systematic
;
Tetrafluoro-N-phenylphthalimide
;
_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
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.0960(14)
_cell_length_b                   8.4060(17)
_cell_length_c                   20.068(4)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      13
_cell_measurement_theta_min      10
_cell_volume                     1197.0(4)
_computing_cell_refinement       'CAD-4 Software'
_computing_data_collection       'CAD-4 Software (Enraf--Nonius, 1985)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'SHELXTL (Bruker, 2000)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       ω/2θ
_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  0.0317
_diffrn_reflns_av_sigmaI/netI    0.0349
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2348
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         2.03
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.152
_exptl_absorpt_correction_T_max  0.985
_exptl_absorpt_correction_T_min  0.955
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al.,  1968)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.638
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.149
_refine_diff_density_min         -0.161
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         1388
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0475
_refine_ls_R_factor_gt           0.0351
_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)+(0.05P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0834
_refine_ls_wR_factor_ref         0.0898
_reflns_number_gt                1079
_reflns_number_total             1388
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hk2269.cif
_cod_data_source_block           I
_cod_database_code               2214259
_cod_database_fobs_code          2214259
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
F F1 0.7900(3) 1.1852(2) -0.18876(8) 0.0824(6) Uani d . 1
F F2 0.4777(3) 1.2338(2) -0.11603(10) 0.0814(7) Uani d . 1
F F3 0.4567(2) 1.1333(2) 0.01142(9) 0.0673(5) Uani d . 1
F F4 1.0865(3) 1.0230(2) -0.13876(8) 0.0734(6) Uani d . 1
O O1 1.2119(3) 0.8510(2) -0.01010(9) 0.0576(5) Uani d . 1
O O2 0.6970(3) 0.9697(3) 0.11857(9) 0.0606(5) Uani d . 1
N N 0.9795(3) 0.8960(3) 0.06903(10) 0.0454(5) Uani d . 1
C C1 1.0590(6) 0.6500(4) 0.21979(15) 0.0730(10) Uani d . 1
H H1A 0.9942 0.5770 0.2460 0.088 Uiso calc R 1
C C2 0.9740(5) 0.7132(4) 0.16367(15) 0.0605(8) Uani d . 1
H H2A 0.8535 0.6809 0.1514 0.073 Uiso calc R 1
C C3 1.0692(4) 0.8240(3) 0.12618(12) 0.0470(6) Uani d . 1
C C4 1.2493(4) 0.8701(4) 0.14324(14) 0.0566(8) Uani d . 1
H H4A 1.3134 0.9445 0.1175 0.068 Uiso calc R 1
C C5 1.3328(5) 0.8057(4) 0.19844(14) 0.0682(9) Uani d . 1
H H5A 1.4542 0.8366 0.2102 0.082 Uiso calc R 1
C C6 1.2381(6) 0.6949(5) 0.23682(15) 0.0754(10) Uani d . 1
H H6A 1.2959 0.6509 0.2741 0.090 Uiso calc R 1
C C7 0.7977(4) 0.9623(3) 0.07029(13) 0.0478(6) Uani d . 1
C C8 1.0603(4) 0.9040(3) 0.00558(13) 0.0461(6) Uani d . 1
C C9 0.9221(4) 0.9915(3) -0.03620(13) 0.0450(6) Uani d . 1
C C10 0.7641(4) 1.0220(3) 0.00212(12) 0.0457(6) Uani d . 1
C C11 0.6128(4) 1.1016(3) -0.02440(15) 0.0511(7) Uani d . 1
C C12 0.6241(4) 1.1549(3) -0.08918(15) 0.0574(8) Uani d . 1
C C13 0.7831(5) 1.1282(4) -0.12682(14) 0.0582(8) Uani d . 1
C C14 0.9322(4) 1.0455(3) -0.10040(14) 0.0536(7) Uani d . 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0000 '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_publ_flag
C8 N C7 112.0(2) yes
C8 N C3 124.2(2) yes
C7 N C3 123.8(2) yes
C6 C1 C2 120.1(3) ?
C6 C1 H1A 119.9 ?
C2 C1 H1A 119.9 ?
C3 C2 C1 119.4(3) ?
C3 C2 H2A 120.3 ?
C1 C2 H2A 120.3 ?
C2 C3 C4 120.7(3) ?
C2 C3 N 120.1(3) yes
C4 C3 N 119.2(3) yes
C5 C4 C3 119.4(3) ?
C5 C4 H4A 120.3 ?
C3 C4 H4A 120.3 ?
C4 C5 C6 120.5(3) ?
C4 C5 H5A 119.8 ?
C6 C5 H5A 119.8 ?
C1 C6 C5 119.9(3) ?
C1 C6 H6A 120.1 ?
C5 C6 H6A 120.1 ?
O2 C7 N 125.4(3) yes
O2 C7 C10 129.1(3) yes
N C7 C10 105.5(2) yes
O1 C8 N 125.9(3) yes
O1 C8 C9 128.6(3) yes
N C8 C9 105.5(2) yes
C14 C9 C10 120.3(3) ?
C14 C9 C8 131.4(3) ?
C10 C9 C8 108.2(2) ?
C11 C10 C9 120.6(2) ?
C11 C10 C7 130.6(2) ?
C9 C10 C7 108.7(2) ?
F3 C11 C10 122.2(3) yes
F3 C11 C12 119.2(3) yes
C10 C11 C12 118.6(3) ?
F2 C12 C13 119.6(3) yes
F2 C12 C11 119.6(3) yes
C13 C12 C11 120.9(3) ?
F1 C13 C14 120.9(3) yes
F1 C13 C12 118.9(3) yes
C14 C13 C12 120.2(3) ?
F4 C14 C9 122.2(3) yes
F4 C14 C13 118.4(2) yes
C9 C14 C13 119.4(3) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
F1 C13 1.333(3) yes
F2 C12 1.345(3) yes
F3 C11 1.347(3) yes
F4 C14 1.352(3) yes
O1 C8 1.206(3) yes
O2 C7 1.206(3) yes
N C8 1.398(3) yes
N C7 1.405(4) yes
N C3 1.445(3) yes
C1 C6 1.369(5) ?
C1 C2 1.383(5) ?
C1 H1A 0.9300 ?
C2 C3 1.375(4) ?
C2 H2A 0.9300 ?
C3 C4 1.379(4) ?
C4 C5 1.368(4) ?
C4 H4A 0.9300 ?
C5 C6 1.383(5) ?
C5 H5A 0.9300 ?
C6 H6A 0.9300 ?
C7 C10 1.477(4) ?
C8 C9 1.485(4) ?
C9 C14 1.368(4) ?
C9 C10 1.384(3) ?
C10 C11 1.373(4) ?
C11 C12 1.377(4) ?
C12 C13 1.376(4) ?
C13 C14 1.373(4) ?
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
C6 C1 C2 C3 -1.6(5)
C1 C2 C3 C4 1.3(4)
C1 C2 C3 N -177.4(3)
C8 N C3 C2 -129.0(3)
C7 N C3 C2 49.0(4)
C8 N C3 C4 52.3(4)
C7 N C3 C4 -129.7(3)
C2 C3 C4 C5 -0.6(4)
N C3 C4 C5 178.1(3)
C3 C4 C5 C6 0.2(5)
C2 C1 C6 C5 1.2(6)
C4 C5 C6 C1 -0.5(5)
C8 N C7 O2 179.6(3)
C3 N C7 O2 1.4(4)
C8 N C7 C10 -2.1(3)
C3 N C7 C10 179.7(2)
C7 N C8 O1 -177.2(3)
C3 N C8 O1 1.0(5)
C7 N C8 C9 3.5(3)
C3 N C8 C9 -178.3(2)
O1 C8 C9 C14 -5.5(5)
N C8 C9 C14 173.8(3)
O1 C8 C9 C10 177.0(3)
N C8 C9 C10 -3.7(3)
C14 C9 C10 C11 2.4(4)
C8 C9 C10 C11 -179.8(2)
C14 C9 C10 C7 -175.3(2)
C8 C9 C10 C7 2.5(3)
O2 C7 C10 C11 0.5(5)
N C7 C10 C11 -177.8(3)
O2 C7 C10 C9 177.9(3)
N C7 C10 C9 -0.4(3)
C9 C10 C11 F3 180.0(2)
C7 C10 C11 F3 -2.9(5)
C9 C10 C11 C12 -2.1(4)
C7 C10 C11 C12 175.1(3)
F3 C11 C12 F2 -1.7(4)
C10 C11 C12 F2 -179.7(3)
F3 C11 C12 C13 178.4(3)
C10 C11 C12 C13 0.4(4)
F2 C12 C13 F1 1.8(4)
C11 C12 C13 F1 -178.4(3)
F2 C12 C13 C14 -178.9(3)
C11 C12 C13 C14 1.0(5)
C10 C9 C14 F4 177.7(3)
C8 C9 C14 F4 0.5(5)
C10 C9 C14 C13 -1.0(4)
C8 C9 C14 C13 -178.2(3)
F1 C13 C14 F4 -0.1(5)
C12 C13 C14 F4 -179.4(3)
F1 C13 C14 C9 178.6(3)
C12 C13 C14 C9 -0.7(5)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 412512
