#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/03/2210384.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_2210384
loop_
_publ_author_name
'Odabaşoğlu, Mustafa'
'Büyükgüngör, Orhan'
_publ_section_title
;
 3-[2-(Trifluoromethyl)anilino]isobenzofuran-1(3H)-one
;
_journal_coeditor_code           SJ2103
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o4148
_journal_page_last               o4150
_journal_paper_doi               10.1107/S1600536806032582
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C15 H10 F3 N O2'
_chemical_formula_moiety         'C15 H10 F3 N O2'
_chemical_formula_sum            'C15 H10 F3 N O2'
_chemical_formula_weight         293.24
_chemical_name_common            3-[2-(trifluoromethyl)anilino]phthalide
_chemical_name_systematic
;
3-[2-(trifluoromethyl)anilino]isobenzofuran-1(3H)-one
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_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                 105.072(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.6389(9)
_cell_length_b                   7.7222(5)
_cell_length_c                   17.3829(15)
_cell_measurement_reflns_used    16157
_cell_measurement_temperature    296
_cell_measurement_theta_max      27.95
_cell_measurement_theta_min      2.19
_cell_volume                     1249.36(18)
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0810
_diffrn_reflns_av_sigmaI/netI    0.0425
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            16157
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.19
_diffrn_standards_decay_%        <2
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.134
_exptl_absorpt_correction_T_max  0.9638
_exptl_absorpt_correction_T_min  0.7459
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   '(X-RED; Stoe & Cie, 2002)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.559
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.58
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.213
_refine_diff_density_min         -0.298
_refine_ls_extinction_coef       0.0105(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     195
_refine_ls_number_reflns         2462
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0668
_refine_ls_R_factor_gt           0.0430
_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)+(0.0486P)²+0.2157P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1021
_refine_ls_wR_factor_ref         0.1129
_reflns_number_gt                1750
_reflns_number_total             2462
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sj2103.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2210384
_cod_database_fobs_code          2210384
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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 0.5424(2) 0.2231(3) 0.33628(11) 0.0507(5) Uani d . 1
C C2 0.5873(2) 0.4017(3) 0.35845(11) 0.0469(5) Uani d . 1
C C3 0.5299(2) 0.5220(3) 0.40051(12) 0.0567(6) Uani d . 1
H H3 0.4527 0.4942 0.4210 0.068 Uiso calc R 1
C C4 0.5908(3) 0.6839(3) 0.41089(13) 0.0646(6) Uani d . 1
H H4 0.5540 0.7675 0.4387 0.078 Uiso calc R 1
C C5 0.7063(3) 0.7246(3) 0.38063(13) 0.0617(6) Uani d . 1
H H5 0.7451 0.8355 0.3880 0.074 Uiso calc R 1
C C6 0.7653(3) 0.6029(3) 0.33955(12) 0.0526(5) Uani d . 1
H H6 0.8433 0.6299 0.3196 0.063 Uiso calc R 1
C C7 0.7037(2) 0.4404(2) 0.32954(11) 0.0446(5) Uani d . 1
C C8 0.7454(2) 0.2817(2) 0.29103(11) 0.0457(5) Uani d . 1
H H8 0.8376 0.2393 0.3239 0.055 Uiso calc R 1
C C9 0.8040(2) 0.1739(2) 0.17147(11) 0.0431(4) Uani d . 1
C C10 0.8268(2) 0.1994(2) 0.09560(10) 0.0423(4) Uani d . 1
C C11 0.8643(2) 0.0612(2) 0.05451(11) 0.0482(5) Uani d . 1
H H11 0.8756 0.0788 0.0036 0.058 Uiso calc R 1
C C12 0.8852(2) -0.1016(3) 0.08743(12) 0.0518(5) Uani d . 1
H H12 0.9096 -0.1936 0.0590 0.062 Uiso calc R 1
C C13 0.8695(2) -0.1264(3) 0.16288(12) 0.0536(5) Uani d . 1
H H13 0.8864 -0.2353 0.1863 0.064 Uiso calc R 1
C C14 0.8291(2) 0.0080(3) 0.20431(12) 0.0509(5) Uani d . 1
H H14 0.8183 -0.0120 0.2552 0.061 Uiso calc R 1
C C15 0.8163(3) 0.3735(3) 0.05909(12) 0.0548(5) Uani d . 1
N N1 0.7575(2) 0.3078(2) 0.21261(9) 0.0470(4) Uani d . 1
O O1 0.44588(19) 0.1394(2) 0.34948(10) 0.0699(5) Uani d . 1
O O2 0.63214(16) 0.15582(17) 0.29525(8) 0.0534(4) Uani d . 1
F F1 0.6923(2) 0.4511(2) 0.05127(11) 0.1048(7) Uani d . 1
F F2 0.9138(2) 0.48203(19) 0.10258(10) 0.1058(7) Uani d . 1
F F3 0.84048(19) 0.37478(17) -0.01280(8) 0.0813(5) Uani d . 1
H H1 0.705(2) 0.392(3) 0.1843(13) 0.058(6) 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 121.63(19) y
O1 C1 C2 130.2(2) y
O2 C1 C2 108.19(17) ?
C7 C2 C3 121.5(2) ?
C7 C2 C1 108.75(17) ?
C3 C2 C1 129.7(2) ?
C4 C3 C2 117.7(2) ?
C4 C3 H3 121.1 ?
C2 C3 H3 121.1 ?
C3 C4 C5 121.0(2) ?
C3 C4 H4 119.5 ?
C5 C4 H4 119.5 ?
C4 C5 C6 121.3(2) ?
C4 C5 H5 119.4 ?
C6 C5 H5 119.4 ?
C7 C6 C5 117.4(2) ?
C7 C6 H6 121.3 ?
C5 C6 H6 121.3 ?
C2 C7 C6 121.09(18) ?
C2 C7 C8 108.91(17) ?
C6 C7 C8 129.99(19) ?
N1 C8 O2 112.91(15) y
N1 C8 C7 114.40(16) ?
O2 C8 C7 103.19(15) ?
N1 C8 H8 108.7 ?
O2 C8 H8 108.7 ?
C7 C8 H8 108.7 ?
N1 C9 C14 120.97(17) ?
N1 C9 C10 121.74(16) ?
C14 C9 C10 117.29(17) ?
C11 C10 C9 120.10(17) ?
C11 C10 C15 118.56(17) ?
C9 C10 C15 121.31(16) ?
C12 C11 C10 121.37(18) ?
C12 C11 H11 119.3 ?
C10 C11 H11 119.3 ?
C13 C12 C11 119.04(18) ?
C13 C12 H12 120.5 ?
C11 C12 H12 120.5 ?
C12 C13 C14 120.74(19) ?
C12 C13 H13 119.6 ?
C14 C13 H13 119.6 ?
C13 C14 C9 121.35(18) ?
C13 C14 H14 119.3 ?
C9 C14 H14 119.3 ?
F1 C15 F3 106.09(19) ?
F1 C15 F2 105.08(19) ?
F3 C15 F2 104.91(19) ?
F1 C15 C10 114.77(19) ?
F3 C15 C10 113.61(16) ?
F2 C15 C10 111.54(18) ?
C9 N1 C8 120.45(16) ?
C9 N1 H1 117.9(14) ?
C8 N1 H1 117.6(14) ?
C1 O2 C8 110.73(14) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 O1 1.202(2) y
C1 O2 1.359(2) y
C1 C2 1.467(3) ?
C2 C7 1.376(3) y
C2 C3 1.384(3) ?
C3 C4 1.372(3) ?
C3 H3 0.9300 ?
C4 C5 1.386(3) ?
C4 H4 0.9300 ?
C5 C6 1.388(3) ?
C5 H5 0.9300 ?
C6 C7 1.380(3) ?
C6 H6 0.9300 ?
C7 C8 1.500(3) ?
C8 N1 1.412(2) ?
C8 O2 1.478(2) ?
C8 H8 0.9800 ?
C9 N1 1.396(2) y
C9 C14 1.398(3) ?
C9 C10 1.406(3) ?
C10 C11 1.384(3) ?
C10 C15 1.479(3) ?
C11 C12 1.374(3) ?
C11 H11 0.9300 ?
C12 C13 1.372(3) ?
C12 H12 0.9300 ?
C13 C14 1.376(3) ?
C13 H13 0.9300 ?
C14 H14 0.9300 ?
C15 F1 1.311(3) ?
C15 F3 1.330(2) ?
C15 F2 1.337(3) ?
N1 H1 0.89(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 F1 . 0.89(2) 2.33(2) 2.927(2) 124.9(18)
C14 H14 O2 . 0.93 2.46 2.994(3) 117
N1 H1 O1 2_655 0.89(2) 2.38(2) 3.235(2) 160.9(19)
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 -179.8(2)
O2 C1 C2 C7 0.6(2)
O1 C1 C2 C3 -0.2(4)
O2 C1 C2 C3 -179.83(19)
C7 C2 C3 C4 1.6(3)
C1 C2 C3 C4 -178.0(2)
C2 C3 C4 C5 -0.4(3)
C3 C4 C5 C6 -0.7(3)
C4 C5 C6 C7 0.5(3)
C3 C2 C7 C6 -1.8(3)
C1 C2 C7 C6 177.82(18)
C3 C2 C7 C8 176.86(18)
C1 C2 C7 C8 -3.5(2)
C5 C6 C7 C2 0.7(3)
C5 C6 C7 C8 -177.63(19)
C2 C7 C8 N1 127.92(19)
C6 C7 C8 N1 -53.6(3)
C2 C7 C8 O2 4.9(2)
C6 C7 C8 O2 -176.62(19)
N1 C9 C10 C11 -175.98(19)
C14 C9 C10 C11 3.7(3)
N1 C9 C10 C15 6.0(3)
C14 C9 C10 C15 -174.3(2)
C9 C10 C11 C12 -2.4(3)
C15 C10 C11 C12 175.6(2)
C10 C11 C12 C13 -0.5(3)
C11 C12 C13 C14 2.0(3)
C12 C13 C14 C9 -0.6(3)
N1 C9 C14 C13 177.4(2)
C10 C9 C14 C13 -2.3(3)
C11 C10 C15 F1 124.5(2)
C9 C10 C15 F1 -57.5(3)
C11 C10 C15 F3 2.2(3)
C9 C10 C15 F3 -179.81(19)
C11 C10 C15 F2 -116.2(2)
C9 C10 C15 F2 61.9(3)
C14 C9 N1 C8 4.9(3)
C10 C9 N1 C8 -175.43(19)
O2 C8 N1 C9 -66.3(2)
C7 C8 N1 C9 176.12(18)
O1 C1 O2 C8 -177.00(19)
C2 C1 O2 C8 2.7(2)
N1 C8 O2 C1 -128.62(18)
C7 C8 O2 C1 -4.6(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 2404875
