#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/94/2209479.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_2209479
loop_
_publ_author_name
'Odabaşoğlu, Mustafa'
'Büyükgüngör, Orhan'
_publ_section_title
;
 3-Anilinoisobenzofuran-1(3H)-one
;
_journal_coeditor_code           DN2048
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2943
_journal_page_last               o2944
_journal_paper_doi               10.1107/S1600536806022537
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C14 H11 N O2'
_chemical_formula_moiety         'C14 H11 N O2'
_chemical_formula_sum            'C14 H11 N O2'
_chemical_formula_weight         225.24
_chemical_name_common            3-anilinophthalide
_chemical_name_systematic
;
3-anilinoisobenzofuran-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                 128.525(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.5710(14)
_cell_length_b                   7.0258(6)
_cell_length_c                   15.7581(15)
_cell_measurement_reflns_used    9007
_cell_measurement_temperature    296
_cell_measurement_theta_max      27.78
_cell_measurement_theta_min      2.06
_cell_volume                     1088.8(2)
_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, 1997)'
_diffrn_ambient_temperature      296
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Stoe IPDS-2'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_source
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0383
_diffrn_reflns_av_sigmaI/netI    0.0366
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            7405
_diffrn_reflns_theta_full        25.97
_diffrn_reflns_theta_max         25.97
_diffrn_reflns_theta_min         2.07
_diffrn_standards_decay_%        2
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  0.9932
_exptl_absorpt_correction_T_min  0.9693
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   '(X-RED32; Stoe & Cie, 2002)'
_exptl_crystal_colour            'light brown'
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.133
_refine_diff_density_min         -0.101
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     157
_refine_ls_number_reflns         2109
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.009
_refine_ls_R_factor_all          0.0614
_refine_ls_R_factor_gt           0.0354
_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)+(0.043P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0762
_refine_ls_wR_factor_ref         0.0840
_reflns_number_gt                1457
_reflns_number_total             2109
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            dn2048.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2209479
_cod_database_fobs_code          2209479
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 0.55578(17) 0.6667(2) 0.31536(13) 0.0457(4) Uani d . 1
C C2 0.52436(16) 0.70687(19) 0.38900(12) 0.0431(3) Uani d . 1
C C3 0.61107(19) 0.7431(2) 0.49902(14) 0.0534(4) Uani d . 1
H H3 0.7047 0.7492 0.5377 0.064 Uiso calc R 1
C C4 0.5536(2) 0.7699(2) 0.54939(14) 0.0600(5) Uani d . 1
H H4 0.6094 0.7920 0.6237 0.072 Uiso calc R 1
C C5 0.4143(2) 0.7641(2) 0.49068(14) 0.0583(5) Uani d . 1
H H5 0.3779 0.7842 0.5263 0.070 Uiso calc R 1
C C6 0.32817(18) 0.7295(2) 0.38096(13) 0.0511(4) Uani d . 1
H H6 0.2344 0.7270 0.3419 0.061 Uiso calc R 1
C C7 0.38567(16) 0.69855(19) 0.33066(12) 0.0423(3) Uani d . 1
C C8 0.32010(15) 0.6425(2) 0.21569(12) 0.0443(3) Uani d . 1
H H8 0.2783 0.5167 0.2012 0.053 Uiso calc R 1
C C9 0.13879(15) 0.7277(2) 0.02572(12) 0.0435(4) Uani d . 1
C C10 0.06764(17) 0.8744(2) -0.04856(14) 0.0555(4) Uani d . 1
H H10 0.0828 0.9996 -0.0243 0.067 Uiso calc R 1
C C11 -0.02506(19) 0.8361(3) -0.15777(15) 0.0648(5) Uani d . 1
H H11 -0.0739 0.9353 -0.2065 0.078 Uiso calc R 1
C C12 -0.04608(19) 0.6521(3) -0.19547(14) 0.0658(5) Uani d . 1
H H12 -0.1089 0.6264 -0.2693 0.079 Uiso calc R 1
C C13 0.02688(18) 0.5074(3) -0.12273(14) 0.0589(4) Uani d . 1
H H13 0.0141 0.3831 -0.1478 0.071 Uiso calc R 1
C C14 0.11879(17) 0.5433(2) -0.01315(13) 0.0513(4) Uani d . 1
H H14 0.1677 0.4435 0.0351 0.062 Uiso calc R 1
N N1 0.22283(14) 0.77089(19) 0.13675(11) 0.0482(3) Uani d . 1
H H1 0.2453(17) 0.892(3) 0.1521(14) 0.058 Uiso d . 1
O O1 0.66471(11) 0.66527(16) 0.33351(10) 0.0589(3) Uani d . 1
O O2 0.43964(11) 0.62763(15) 0.21637(8) 0.0517(3) 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 0.0016 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O1 C1 O2 121.57(14)
O1 C1 C2 129.50(16)
O2 C1 C2 108.93(13)
C7 C2 C3 121.88(14)
C7 C2 C1 108.47(13)
C3 C2 C1 129.63(15)
C4 C3 C2 117.48(17)
C4 C3 H3 121.3
C2 C3 H3 121.3
C3 C4 C5 120.72(16)
C3 C4 H4 119.6
C5 C4 H4 119.6
C6 C5 C4 121.65(15)
C6 C5 H5 119.2
C4 C5 H5 119.2
C5 C6 C7 117.73(16)
C5 C6 H6 121.1
C7 C6 H6 121.1
C2 C7 C6 120.52(14)
C2 C7 C8 109.40(12)
C6 C7 C8 129.98(14)
N1 C8 O2 111.60(11)
N1 C8 C7 114.97(12)
O2 C8 C7 102.41(11)
N1 C8 H8 109.2
O2 C8 H8 109.2
C7 C8 H8 109.2
C14 C9 C10 118.46(14)
C14 C9 N1 122.78(14)
C10 C9 N1 118.69(14)
C11 C10 C9 120.54(16)
C11 C10 H10 119.7
C9 C10 H10 119.7
C10 C11 C12 120.54(17)
C10 C11 H11 119.7
C12 C11 H11 119.7
C13 C12 C11 119.12(17)
C13 C12 H12 120.4
C11 C12 H12 120.4
C12 C13 C14 120.97(17)
C12 C13 H13 119.5
C14 C13 H13 119.5
C13 C14 C9 120.32(15)
C13 C14 H14 119.8
C9 C14 H14 119.8
C8 N1 C9 122.09(13)
C8 N1 H1 115.1(11)
C9 N1 H1 114.5(11)
C1 O2 C8 110.72(11)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O1 1.2121(18)
C1 O2 1.3428(19)
C1 C2 1.467(2)
C2 C7 1.375(2)
C2 C3 1.380(2)
C3 C4 1.379(2)
C3 H3 0.9300
C4 C5 1.381(3)
C4 H4 0.9300
C5 C6 1.374(2)
C5 H5 0.9300
C6 C7 1.3827(19)
C6 H6 0.9300
C7 C8 1.502(2)
C8 N1 1.400(2)
C8 O2 1.4996(17)
C8 H8 0.9800
C9 C14 1.387(2)
C9 C10 1.389(2)
C9 N1 1.403(2)
C10 C11 1.376(2)
C10 H10 0.9300
C11 C12 1.378(3)
C11 H11 0.9300
C12 C13 1.371(3)
C12 H12 0.9300
C13 C14 1.377(2)
C13 H13 0.9300
C14 H14 0.9300
N1 H1 0.880(18)
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_655 0.880(18) 2.169(18) 3.0117(17) 160.2(14)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 2140003
