#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/89/2208919.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_2208919
loop_
_publ_author_name
'Odabaşoğlu, Mustafa'
'Büyükgüngör, Orhan'
_publ_section_title
;
 3-(2-Pyridylamino)isobenzofuran-1(3H)-one
;
_journal_coeditor_code           IS2028
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2079
_journal_page_last               o2080
_journal_paper_doi               10.1107/S1600536806014747
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C13 H10 N2 O2'
_chemical_formula_moiety         'C13 H10 N2 O2'
_chemical_formula_sum            'C13 H10 N2 O2'
_chemical_formula_weight         226.23
_chemical_name_common            3-(2-pyridylamino)phthalide
_chemical_name_systematic
;
3-(2-pyridylamino)isobenzofuran-1(3H)-one
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   8.6366(5)
_cell_length_b                   18.1462(12)
_cell_length_c                   14.3885(11)
_cell_measurement_reflns_used    21419
_cell_measurement_temperature    296
_cell_measurement_theta_max      27.23
_cell_measurement_theta_min      2.25
_cell_volume                     2255.0(3)
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Stoe IPDS-2'
_diffrn_measurement_method       'ω scan rotation method'
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1537
_diffrn_reflns_av_sigmaI/netI    0.0563
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            23991
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.24
_diffrn_standards_decay_%        <2
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.9960
_exptl_absorpt_correction_T_min  0.9614
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   '(X-RED32; Stoe & Cie, 2002)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'prismatic stick'
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.78
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.163
_refine_diff_density_min         -0.181
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     158
_refine_ls_number_reflns         1991
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.1158
_refine_ls_R_factor_gt           0.0622
_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)+(0.0522P)²+0.1489P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1124
_refine_ls_wR_factor_ref         0.1316
_reflns_number_gt                1173
_reflns_number_total             1991
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            is2028.cif
_cod_data_source_block           I
_cod_database_code               2208919
_cod_database_fobs_code          2208919
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, 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 0.3523(5) 0.54681(18) 0.0607(3) 0.0628(9) Uani d . 1
C C2 0.2590(4) 0.48496(17) 0.0953(2) 0.0529(8) Uani d . 1
C C3 0.1734(5) 0.4340(2) 0.0462(3) 0.0728(11) Uani d . 1
H H3 0.1684 0.4352 -0.0184 0.087 Uiso calc R 1
C C4 0.0950(5) 0.3810(2) 0.0971(3) 0.0797(11) Uani d . 1
H H4 0.0356 0.3459 0.0663 0.096 Uiso calc R 1
C C5 0.1038(4) 0.37948(18) 0.1928(3) 0.0676(10) Uani d . 1
H H5 0.0512 0.3429 0.2252 0.081 Uiso calc R 1
C C6 0.1892(4) 0.43105(16) 0.2414(2) 0.0541(8) Uani d . 1
H H6 0.1945 0.4301 0.3060 0.065 Uiso calc R 1
C C7 0.2665(4) 0.48422(16) 0.1904(2) 0.0439(7) Uani d . 1
C C8 0.3644(4) 0.54791(16) 0.2221(2) 0.0484(8) Uani d . 1
H H8 0.4551 0.5294 0.2557 0.058 Uiso calc R 1
C C9 0.3543(4) 0.65661(15) 0.3229(2) 0.0438(7) Uani d . 1
C C10 0.2658(4) 0.71041(16) 0.3667(2) 0.0527(8) Uani d . 1
H H10 0.1583 0.7076 0.3661 0.063 Uiso calc R 1
C C11 0.3390(4) 0.76759(18) 0.4107(2) 0.0610(9) Uani d . 1
H H11 0.2817 0.8043 0.4398 0.073 Uiso calc R 1
C C12 0.4991(4) 0.77010(18) 0.4112(2) 0.0609(9) Uani d . 1
H H12 0.5517 0.8085 0.4402 0.073 Uiso calc R 1
C C13 0.5774(4) 0.71443(17) 0.3679(2) 0.0563(8) Uani d . 1
H H13 0.6851 0.7158 0.3692 0.068 Uiso calc R 1
N N1 0.2816(3) 0.59796(14) 0.27937(19) 0.0495(7) Uani d . 1
N N2 0.5097(3) 0.65780(14) 0.32353(18) 0.0506(7) Uani d . 1
O O1 0.3760(4) 0.56746(14) -0.01803(18) 0.0930(10) Uani d . 1
O O2 0.4143(3) 0.58324(11) 0.13471(16) 0.0620(6) Uani d . 1
H H1 0.188(5) 0.6079(18) 0.256(3) 0.075(11) 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'
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 120.9(3) y
O1 C1 C2 130.3(4) y
O2 C1 C2 108.8(3) ?
C7 C2 C3 122.0(3) ?
C7 C2 C1 108.7(3) ?
C3 C2 C1 129.3(3) ?
C2 C3 C4 117.1(3) ?
C2 C3 H3 121.4 ?
C4 C3 H3 121.4 ?
C5 C4 C3 121.0(4) ?
C5 C4 H4 119.5 ?
C3 C4 H4 119.5 ?
C4 C5 C6 121.4(4) ?
C4 C5 H5 119.3 ?
C6 C5 H5 119.3 ?
C5 C6 C7 117.4(3) ?
C5 C6 H6 121.3 ?
C7 C6 H6 121.3 ?
C2 C7 C6 121.0(3) ?
C2 C7 C8 108.8(3) ?
C6 C7 C8 130.2(3) ?
N1 C8 O2 111.3(2) y
N1 C8 C7 112.6(3) ?
O2 C8 C7 103.8(2) ?
N1 C8 H8 109.6 ?
O2 C8 H8 109.6 ?
C7 C8 H8 109.6 ?
N2 C9 N1 117.9(3) ?
N2 C9 C10 122.4(3) ?
N1 C9 C10 119.7(3) ?
C11 C10 C9 119.2(3) ?
C11 C10 H10 120.4 ?
C9 C10 H10 120.4 ?
C10 C11 C12 119.2(3) ?
C10 C11 H11 120.4 ?
C12 C11 H11 120.4 ?
C13 C12 C11 117.9(3) ?
C13 C12 H12 121.0 ?
C11 C12 H12 121.0 ?
N2 C13 C12 124.5(3) ?
N2 C13 H13 117.7 ?
C12 C13 H13 117.7 ?
C9 N1 C8 121.7(3) ?
C9 N1 H1 115(2) ?
C8 N1 H1 112(2) ?
C9 N2 C13 116.8(3) ?
C1 O2 C8 109.9(2) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 O1 1.211(4) y
C1 O2 1.363(4) y
C1 C2 1.468(5) ?
C2 C7 1.370(4) y
C2 C3 1.378(5) ?
C3 C4 1.386(5) ?
C3 H3 0.9300 ?
C4 C5 1.378(5) ?
C4 H4 0.9300 ?
C5 C6 1.382(5) ?
C5 H5 0.9300 ?
C6 C7 1.384(4) ?
C6 H6 0.9300 ?
C7 C8 1.503(4) y
C8 N1 1.419(4) y
C8 O2 1.476(4) ?
C8 H8 0.9800 ?
C9 N2 1.343(4) ?
C9 N1 1.385(4) ?
C9 C10 1.390(4) ?
C10 C11 1.370(4) ?
C10 H10 0.9300 ?
C11 C12 1.383(5) ?
C11 H11 0.9300 ?
C12 C13 1.366(5) ?
C12 H12 0.9300 ?
C13 N2 1.344(4) ?
C13 H13 0.9300 ?
N1 H1 0.89(4) ?
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 N2 6_556 0.89(4) 2.12(4) 2.981(4) 161(3)
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 -179.4(4)
O2 C1 C2 C7 -0.4(4)
O1 C1 C2 C3 -0.1(7)
O2 C1 C2 C3 178.9(3)
C7 C2 C3 C4 -0.5(6)
C1 C2 C3 C4 -179.7(4)
C2 C3 C4 C5 -0.4(6)
C3 C4 C5 C6 0.8(6)
C4 C5 C6 C7 -0.4(5)
C3 C2 C7 C6 1.0(5)
C1 C2 C7 C6 -179.7(3)
C3 C2 C7 C8 -178.2(3)
C1 C2 C7 C8 1.1(4)
C5 C6 C7 C2 -0.5(5)
C5 C6 C7 C8 178.5(3)
C2 C7 C8 N1 119.2(3)
C6 C7 C8 N1 -59.9(4)
C2 C7 C8 O2 -1.4(3)
C6 C7 C8 O2 179.5(3)
N2 C9 C10 C11 1.3(5)
N1 C9 C10 C11 179.1(3)
C9 C10 C11 C12 -0.6(5)
C10 C11 C12 C13 -0.5(5)
C11 C12 C13 N2 1.0(5)
N2 C9 N1 C8 -11.8(4)
C10 C9 N1 C8 170.4(3)
O2 C8 N1 C9 -69.9(4)
C7 C8 N1 C9 173.9(3)
N1 C9 N2 C13 -178.6(3)
C10 C9 N2 C13 -0.8(5)
C12 C13 N2 C9 -0.3(5)
O1 C1 O2 C8 178.6(3)
C2 C1 O2 C8 -0.5(4)
N1 C8 O2 C1 -120.3(3)
C7 C8 O2 C1 1.1(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 2404904
