#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/03/2210360.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_2210360
loop_
_publ_author_name
'Odabaşoğlu, Mustafa'
'Büyükgüngör, Orhan'
_publ_section_title
;
 3-(4-Fluoroanilino)isobenzofuran-1(3H)-one
;
_journal_coeditor_code           OM2039
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o4138
_journal_page_last               o4139
_journal_paper_doi               10.1107/S1600536806031783
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C14 H10 F N O2'
_chemical_formula_moiety         'C14 H10 F N O2'
_chemical_formula_sum            'C14 H10 F N O2'
_chemical_formula_weight         243.23
_chemical_name_common            3-(4-fluoroanilino)phthalide
_chemical_name_systematic
;
3-(4-fluoroanilino)isobenzofuran-1(3H)-one
;
_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                91.433(9)
_cell_angle_beta                 93.906(9)
_cell_angle_gamma                104.300(9)
_cell_formula_units_Z            2
_cell_length_a                   7.0041(8)
_cell_length_b                   8.1023(9)
_cell_length_c                   10.2114(12)
_cell_measurement_reflns_used    5837
_cell_measurement_temperature    296
_cell_measurement_theta_max      27.87
_cell_measurement_theta_min      3.21
_cell_volume                     559.71(11)
_computing_cell_refinement       X-AREA
_computing_data_collection       'X-AREA (Stoe & Cie, 2002)'
_computing_data_reduction        'X-RED32 (Stoe & Cie, 2002)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'Stoe IPDS-2'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0856
_diffrn_reflns_av_sigmaI/netI    0.0629
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7292
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         3.21
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_T_max  0.9883
_exptl_absorpt_correction_T_min  0.9634
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   '(X-RED32; Stoe & Cie, 2002)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.443
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             252
_exptl_crystal_size_max          0.480
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.110
_refine_diff_density_max         0.159
_refine_diff_density_min         -0.176
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         2202
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.004
_refine_ls_R_factor_all          0.0747
_refine_ls_R_factor_gt           0.0498
_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)+(0.0718P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1227
_refine_ls_wR_factor_ref         0.1333
_reflns_number_gt                1475
_reflns_number_total             2202
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            om2039.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2210360
_cod_database_fobs_code          2210360
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
C C1 0.2513(3) 0.4589(2) 0.55093(19) 0.0478(4) Uani d . 1
C C2 0.2533(3) 0.2814(2) 0.52252(19) 0.0472(4) Uani d . 1
C C3 0.2825(3) 0.1574(3) 0.6068(2) 0.0580(5) Uani d . 1
H H3 0.3079 0.1809 0.6968 0.070 Uiso calc R 1
C C4 0.2727(3) -0.0019(3) 0.5528(2) 0.0638(6) Uani d . 1
H H4 0.2887 -0.0887 0.6071 0.077 Uiso calc R 1
C C5 0.2392(3) -0.0342(3) 0.4189(2) 0.0629(6) Uani d . 1
H H5 0.2351 -0.1426 0.3845 0.075 Uiso calc R 1
C C6 0.2116(3) 0.0898(2) 0.3344(2) 0.0557(5) Uani d . 1
H H6 0.1903 0.0672 0.2441 0.067 Uiso calc R 1
C C7 0.2170(3) 0.2479(2) 0.38889(19) 0.0463(4) Uani d . 1
C C8 0.1799(3) 0.4028(2) 0.32502(18) 0.0477(5) Uani d . 1
H H8 0.0418 0.3779 0.2894 0.057 Uiso calc R 1
C C9 0.2712(3) 0.5906(2) 0.14299(17) 0.0456(4) Uani d . 1
C C10 0.4181(3) 0.6646(2) 0.0633(2) 0.0558(5) Uani d . 1
H H10 0.5386 0.6354 0.0712 0.067 Uiso calc R 1
C C11 0.3894(4) 0.7811(3) -0.0277(2) 0.0666(6) Uani d . 1
H H11 0.4876 0.8284 -0.0824 0.080 Uiso calc R 1
C C12 0.2140(4) 0.8249(3) -0.0353(2) 0.0632(6) Uani d . 1
C C13 0.0670(3) 0.7590(3) 0.0429(2) 0.0612(6) Uani d . 1
H H13 -0.0510 0.7924 0.0359 0.073 Uiso calc R 1
C C14 0.0959(3) 0.6411(3) 0.13331(19) 0.0542(5) Uani d . 1
H H14 -0.0031 0.5956 0.1879 0.065 Uiso calc R 1
N N1 0.3027(3) 0.4624(2) 0.22547(16) 0.0513(4) Uani d . 1
O O1 0.2815(2) 0.53909(19) 0.65512(14) 0.0610(4) Uani d . 1
O O2 0.2102(2) 0.52957(16) 0.43813(13) 0.0522(4) Uani d . 1
F F1 0.1839(3) 0.9402(2) -0.12504(15) 0.0965(5) Uani d . 1
H H1 0.422(3) 0.459(3) 0.2447(19) 0.050(5) Uiso 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 0.0016 '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_publ_flag
O1 C1 O2 121.79(18) y
O1 C1 C2 129.23(18) y
O2 C1 C2 108.97(16) ?
C7 C2 C3 121.58(19) ?
C7 C2 C1 108.42(16) ?
C3 C2 C1 130.00(19) ?
C4 C3 C2 117.6(2) ?
C4 C3 H3 121.2 ?
C2 C3 H3 121.2 ?
C3 C4 C5 120.68(19) ?
C3 C4 H4 119.7 ?
C5 C4 H4 119.7 ?
C4 C5 C6 121.8(2) ?
C4 C5 H5 119.1 ?
C6 C5 H5 119.1 ?
C7 C6 C5 117.4(2) ?
C7 C6 H6 121.3 ?
C5 C6 H6 121.3 ?
C6 C7 C2 120.86(18) ?
C6 C7 C8 129.85(18) ?
C2 C7 C8 109.24(16) ?
N1 C8 O2 111.97(15) y
N1 C8 C7 114.57(16) ?
O2 C8 C7 102.66(14) ?
N1 C8 H8 109.1 ?
O2 C8 H8 109.1 ?
C7 C8 H8 109.1 ?
C10 C9 C14 118.39(18) ?
C10 C9 N1 118.62(17) ?
C14 C9 N1 122.92(18) ?
C11 C10 C9 121.3(2) ?
C11 C10 H10 119.4 ?
C9 C10 H10 119.4 ?
C12 C11 C10 118.3(2) ?
C12 C11 H11 120.9 ?
C10 C11 H11 120.9 ?
C11 C12 C13 122.66(19) ?
C11 C12 F1 118.8(2) ?
C13 C12 F1 118.6(2) ?
C12 C13 C14 118.8(2) ?
C12 C13 H13 120.6 ?
C14 C13 H13 120.6 ?
C9 C14 C13 120.5(2) ?
C9 C14 H14 119.7 ?
C13 C14 H14 119.7 ?
C8 N1 C9 122.22(16) ?
C8 N1 H1 112.5(14) ?
C9 N1 H1 117.3(14) ?
C1 O2 C8 110.63(14) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 O1 1.211(2) y
C1 O2 1.344(2) y
C1 C2 1.464(3) ?
C2 C7 1.378(3) y
C2 C3 1.383(3) ?
C3 C4 1.375(3) ?
C3 H3 0.9300 ?
C4 C5 1.379(3) ?
C4 H4 0.9300 ?
C5 C6 1.381(3) ?
C5 H5 0.9300 ?
C6 C7 1.375(3) ?
C6 H6 0.9300 ?
C7 C8 1.499(2) ?
C8 N1 1.395(2) ?
C8 O2 1.495(2) ?
C8 H8 0.9800 ?
C9 C10 1.383(3) ?
C9 C14 1.385(3) ?
C9 N1 1.404(2) y
C10 C11 1.381(3) ?
C10 H10 0.9300 ?
C11 C12 1.358(3) ?
C11 H11 0.9300 ?
C12 C13 1.358(3) ?
C12 F1 1.368(2) ?
C13 C14 1.385(3) ?
C13 H13 0.9300 ?
C14 H14 0.9300 ?
N1 H1 0.85(2) ?
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
N1 H1 O1 2_666 0.85(2) 2.25(2) 3.082(2) 166.2(18)
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 C7 -177.98(19)
O2 C1 C2 C7 1.5(2)
O1 C1 C2 C3 2.7(3)
O2 C1 C2 C3 -177.8(2)
C7 C2 C3 C4 -0.5(3)
C1 C2 C3 C4 178.75(18)
C2 C3 C4 C5 1.4(3)
C3 C4 C5 C6 -0.9(3)
C4 C5 C6 C7 -0.6(3)
C5 C6 C7 C2 1.5(3)
C5 C6 C7 C8 -175.63(19)
C3 C2 C7 C6 -1.0(3)
C1 C2 C7 C6 179.60(17)
C3 C2 C7 C8 176.66(18)
C1 C2 C7 C8 -2.7(2)
C6 C7 C8 N1 -58.1(3)
C2 C7 C8 N1 124.45(18)
C6 C7 C8 O2 -179.77(18)
C2 C7 C8 O2 2.83(19)
C14 C9 C10 C11 -2.6(3)
N1 C9 C10 C11 174.53(18)
C9 C10 C11 C12 1.5(3)
C10 C11 C12 C13 0.1(3)
C10 C11 C12 F1 180.0(2)
C11 C12 C13 C14 -0.6(3)
F1 C12 C13 C14 179.51(19)
C10 C9 C14 C13 2.0(3)
N1 C9 C14 C13 -174.97(18)
C12 C13 C14 C9 -0.4(3)
O2 C8 N1 C9 -72.7(2)
C7 C8 N1 C9 170.92(16)
C10 C9 N1 C8 168.26(18)
C14 C9 N1 C8 -14.8(3)
O1 C1 O2 C8 179.91(17)
C2 C1 O2 C8 0.41(19)
N1 C8 O2 C1 -125.31(16)
C7 C8 O2 C1 -1.94(18)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 507582
