#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/89/2208982.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_2208982
loop_
_publ_author_name
'Odabaşoğlu, Mustafa'
'Büyükgüngör, Orhan'
_publ_section_title
;
 3-(4-Hydroxyanilino)isobenzofuran-1(3H)-one
;
_journal_coeditor_code           RZ2022
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1879
_journal_page_last               o1881
_journal_paper_doi               10.1107/S1600536806013031
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C14 H11 N O3'
_chemical_formula_moiety         'C14 H11 N O3'
_chemical_formula_sum            'C14 H11 N O3'
_chemical_formula_weight         241.24
_chemical_name_common            3-(p-hydrohxyanilino)phthalide
_chemical_name_systematic
;
3-(4-Hydroxyanilino)isobenzofuran-1(3H)-one
;
_space_group_IT_number           9
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 99.113(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.9049(4)
_cell_length_b                   17.4841(16)
_cell_length_c                   11.7553(8)
_cell_measurement_reflns_used    8507
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.91
_cell_measurement_theta_min      2.33
_cell_volume                     1198.32(16)
_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(2)
_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_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0306
_diffrn_reflns_av_sigmaI/netI    0.0181
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8507
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         2.33
_diffrn_standards_decay_%        <2
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  0.9707
_exptl_absorpt_correction_T_min  0.9400
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   '(X-RED32; Stoe & Cie, 2002)'
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.52
_exptl_crystal_size_min          0.39
_refine_diff_density_max         0.099
_refine_diff_density_min         -0.104
_refine_ls_extinction_coef       0.025(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 1997)'
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     168
_refine_ls_number_reflns         1183
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0263
_refine_ls_R_factor_gt           0.0253
_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)+(0.0458P)²+0.0931P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0659
_refine_ls_wR_factor_ref         0.0666
_reflns_number_gt                1138
_reflns_number_total             1183
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            rz2022.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C c'
_cod_database_code               2208982
_cod_database_fobs_code          2208982
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -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 C2 0.7404(3) 0.21598(10) 0.77051(15) 0.0505(4) Uani d . 1
C C3 0.7108(4) 0.14830(11) 0.82690(17) 0.0623(5) Uani d . 1
H H3 0.8186 0.1314 0.8881 0.075 Uiso calc R 1
C C4 0.5157(4) 0.10686(11) 0.78886(18) 0.0656(5) Uani d . 1
H H4 0.4907 0.0609 0.8246 0.079 Uiso calc R 1
C C5 0.3574(4) 0.13247(12) 0.6988(2) 0.0673(5) Uani d . 1
H H5 0.2256 0.1038 0.6756 0.081 Uiso calc R 1
C C6 0.3886(4) 0.19968(11) 0.64171(17) 0.0606(5) Uani d . 1
H H6 0.2809 0.2164 0.5804 0.073 Uiso calc R 1
C C7 0.5853(3) 0.24110(10) 0.67888(14) 0.0491(4) Uani d . 1
C C8 0.6642(3) 0.31580(10) 0.63582(16) 0.0535(4) Uani d . 1
H H8 0.6968 0.3093 0.5572 0.064 Uiso calc R 1
C C1 0.9226(3) 0.27263(10) 0.79504(16) 0.0565(4) Uani d . 1
C C9 0.5097(3) 0.44376(9) 0.57864(13) 0.0479(4) Uani d . 1
C C10 0.3316(3) 0.49488(11) 0.58353(16) 0.0544(4) Uani d . 1
H H10 0.2227 0.4839 0.6303 0.065 Uiso calc R 1
C C11 0.3133(3) 0.56159(11) 0.52034(16) 0.0545(4) Uani d . 1
H H11 0.1936 0.5954 0.5252 0.065 Uiso calc R 1
C C12 0.4730(3) 0.57820(10) 0.44964(14) 0.0501(4) Uani d . 1
C C13 0.6518(3) 0.52839(10) 0.44534(16) 0.0560(4) Uani d . 1
H H13 0.7604 0.5395 0.3984 0.067 Uiso calc R 1
C C14 0.6720(3) 0.46212(10) 0.50985(16) 0.0541(4) Uani d . 1
H H14 0.7955 0.4295 0.5072 0.065 Uiso calc R 1
N N1 0.5067(3) 0.37439(9) 0.63805(15) 0.0611(4) Uani d . 1
O O1 1.0857(3) 0.27155(9) 0.87252(13) 0.0753(5) Uani d . 1
O O2 0.8869(2) 0.32913(7) 0.71767(12) 0.0613(4) Uani d . 1
O O3 0.4655(3) 0.64365(8) 0.38537(13) 0.0697(4) Uani d . 1
H H3A 0.3525 0.6688 0.3944 0.105 Uiso calc R 1
H H1 0.438(5) 0.3753(13) 0.697(2) 0.068(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 0.0000 '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'
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
C7 C2 C3 122.13(17) ?
C7 C2 C1 108.56(15) y
C3 C2 C1 129.28(17) ?
C4 C3 C2 117.32(18) ?
C4 C3 H3 121.3 ?
C2 C3 H3 121.3 ?
C5 C4 C3 120.83(18) ?
C5 C4 H4 119.6 ?
C3 C4 H4 119.6 ?
C4 C5 C6 121.76(18) ?
C4 C5 H5 119.1 ?
C6 C5 H5 119.1 ?
C7 C6 C5 117.60(18) ?
C7 C6 H6 121.2 ?
C5 C6 H6 121.2 ?
C2 C7 C6 120.33(17) y
C2 C7 C8 109.81(16) y
C6 C7 C8 129.84(17) ?
N1 C8 C7 113.02(17) y
N1 C8 O2 113.01(15) y
C7 C8 O2 101.75(14) y
N1 C8 H8 109.6 ?
C7 C8 H8 109.6 ?
O2 C8 H8 109.6 ?
O1 C1 O2 122.81(17) y
O1 C1 C2 127.58(17) y
O2 C1 C2 109.62(16) ?
C14 C9 C10 118.27(15) ?
C14 C9 N1 123.76(15) ?
C10 C9 N1 117.85(15) ?
C11 C10 C9 121.19(16) ?
C11 C10 H10 119.4 ?
C9 C10 H10 119.4 ?
C10 C11 C12 119.93(16) ?
C10 C11 H11 120.0 ?
C12 C11 H11 120.0 ?
O3 C12 C13 117.86(15) ?
O3 C12 C11 122.80(16) ?
C13 C12 C11 119.31(16) ?
C12 C13 C14 120.76(15) ?
C12 C13 H13 119.6 ?
C14 C13 H13 119.6 ?
C13 C14 C9 120.51(15) ?
C13 C14 H14 119.7 ?
C9 C14 H14 119.7 ?
C8 N1 C9 124.65(16) y
C8 N1 H1 115.8(16) ?
C9 N1 H1 115.6(16) ?
C1 O2 C8 110.18(13) y
C12 O3 H3A 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C2 C7 1.371(2) y
C2 C3 1.381(3) ?
C2 C1 1.457(2) y
C3 C4 1.375(3) ?
C3 H3 0.9300 ?
C4 C5 1.371(3) ?
C4 H4 0.9300 ?
C5 C6 1.380(3) ?
C5 H5 0.9300 ?
C6 C7 1.380(3) ?
C6 H6 0.9300 ?
C7 C8 1.501(2) y
C8 N1 1.387(2) y
C8 O2 1.519(2) y
C8 H8 0.9800 ?
C1 O1 1.216(2) y
C1 O2 1.337(2) ?
C9 C14 1.386(2) ?
C9 C10 1.388(2) ?
C9 N1 1.401(2) y
C10 C11 1.378(3) ?
C10 H10 0.9300 ?
C11 C12 1.383(3) ?
C11 H11 0.9300 ?
C12 O3 1.368(2) y
C12 C13 1.376(2) ?
C13 C14 1.380(2) ?
C13 H13 0.9300 ?
C14 H14 0.9300 ?
N1 H1 0.85(3) ?
O3 H3A 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 H3A O1 2_464 0.82 1.87 2.673(2) 165
N1 H1 O3 2_565 0.85(3) 2.23(3) 2.972(2) 147(2)
C8 H8 O1 4_454 0.98 2.59 3.417(2) 143
C3 H3 Cg2 4_555 0.93 3.00 3.777(2) 142
C5 H5 Cg2 3_455 0.93 2.70 3.513(2) 147
C11 H11 Cg1 3_445 0.93 3.05 3.722(2) 130
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
_geom_torsion_publ_flag
C7 C2 C3 C4 -1.1(3) ?
C1 C2 C3 C4 176.9(2) ?
C2 C3 C4 C5 -0.3(3) ?
C3 C4 C5 C6 1.1(3) ?
C4 C5 C6 C7 -0.5(3) ?
C3 C2 C7 C6 1.7(3) ?
C1 C2 C7 C6 -176.61(17) ?
C3 C2 C7 C8 -179.83(18) ?
C1 C2 C7 C8 1.8(2) ?
C5 C6 C7 C2 -0.9(3) ?
C5 C6 C7 C8 -179.01(19) ?
C2 C7 C8 N1 -121.78(18) ?
C6 C7 C8 N1 56.5(3) ?
C2 C7 C8 O2 -0.31(18) ?
C6 C7 C8 O2 177.94(18) ?
C7 C2 C1 O1 177.2(2) ?
C3 C2 C1 O1 -1.0(3) y
C7 C2 C1 O2 -2.8(2) ?
C3 C2 C1 O2 178.97(19) ?
C14 C9 C10 C11 1.1(3) ?
N1 C9 C10 C11 -175.00(17) ?
C9 C10 C11 C12 0.6(3) ?
C10 C11 C12 O3 -179.52(17) ?
C10 C11 C12 C13 -1.4(3) ?
O3 C12 C13 C14 178.72(16) ?
C11 C12 C13 C14 0.5(3) ?
C12 C13 C14 C9 1.2(3) ?
C10 C9 C14 C13 -2.0(3) ?
N1 C9 C14 C13 173.85(16) ?
C7 C8 N1 C9 -164.02(16) ?
O2 C8 N1 C9 81.1(2) ?
C14 C9 N1 C8 0.1(3) y
C10 C9 N1 C8 175.98(18) ?
O1 C1 O2 C8 -177.37(19) y
C2 C1 O2 C8 2.64(19) ?
N1 C8 O2 C1 120.02(17) ?
C7 C8 O2 C1 -1.47(17) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 451855
