#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/90/2209005.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_2209005
loop_
_publ_author_name
'Odabaşoğlu, Mustafa'
'Büyükgüngör, Orhan'
_publ_section_title
;
 3-(3-Pyridylamino)isobenzofuran-1(3H)-one
;
_journal_coeditor_code           SJ2041
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2088
_journal_page_last               o2089
_journal_paper_doi               10.1107/S1600536806013390
_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-(3-pyridylamino)phthalide
_chemical_name_systematic
;
3-(3-Pyridylamino)isobenzofuran-1(3H)-one
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.8236(5)
_cell_length_b                   7.9820(7)
_cell_length_c                   24.5229(17)
_cell_measurement_reflns_used    1327
_cell_measurement_temperature    296
_cell_measurement_theta_max      27.15
_cell_measurement_theta_min      1.66
_cell_volume                     1139.92(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 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Stoe IPDS-2'
_diffrn_measurement_method       'ω rotation method'
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0395
_diffrn_reflns_av_sigmaI/netI    0.0165
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            9694
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.66
_diffrn_standards_decay_%        <2
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.9923
_exptl_absorpt_correction_T_min  0.9389
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   '(X-RED32; Stoe & Cie, 2002)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'square plate'
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.74
_exptl_crystal_size_mid          0.52
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.111
_refine_diff_density_min         -0.120
_refine_ls_extinction_coef       0.047(8)
_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   1.066
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     159
_refine_ls_number_reflns         1327
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0427
_refine_ls_R_factor_gt           0.0342
_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)+(0.0563P)²+0.0337P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0861
_refine_ls_wR_factor_ref         0.0905
_reflns_number_gt                1110
_reflns_number_total             1327
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sj2041.cif
_cod_data_source_block           I
_cod_database_code               2209005
_cod_database_fobs_code          2209005
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'
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 0.2401(4) 0.2490(3) 0.05503(7) 0.0543(5) Uani d . 1
C C2 0.2727(4) 0.4295(2) 0.06127(7) 0.0522(5) Uani d . 1
C C3 0.1410(5) 0.5606(3) 0.04184(9) 0.0654(6) Uani d . 1
H H3 0.0086 0.5414 0.0216 0.079 Uiso calc R 1
C C4 0.2130(6) 0.7198(3) 0.05356(10) 0.0756(8) Uani d . 1
H H4 0.1288 0.8108 0.0408 0.091 Uiso calc R 1
C C5 0.4089(6) 0.7475(3) 0.08402(10) 0.0790(8) Uani d . 1
H H5 0.4532 0.8570 0.0916 0.095 Uiso calc R 1
C C6 0.5407(5) 0.6165(3) 0.10350(9) 0.0678(6) Uani d . 1
H H6 0.6721 0.6357 0.1241 0.081 Uiso calc R 1
C C7 0.4696(4) 0.4560(2) 0.09120(7) 0.0525(5) Uani d . 1
C C8 0.5744(4) 0.2909(2) 0.10526(8) 0.0536(5) Uani d . 1
H H8 0.7252 0.2809 0.0879 0.064 Uiso calc R 1
C C9 0.6961(4) 0.1211(2) 0.18322(7) 0.0537(5) Uani d . 1
C C10 0.6318(4) 0.0685(3) 0.23493(9) 0.0678(6) Uani d . 1
H H10 0.5170 0.1283 0.2527 0.081 Uiso calc R 1
C C11 0.8877(5) -0.1442(4) 0.23544(11) 0.0820(8) Uani d . 1
H H11 0.9555 -0.2340 0.2534 0.098 Uiso calc R 1
C C12 0.9634(5) -0.1051(3) 0.18464(10) 0.0797(7) Uani d . 1
H H12 1.0799 -0.1671 0.1683 0.096 Uiso calc R 1
C C13 0.8636(5) 0.0293(3) 0.15747(9) 0.0684(6) Uani d . 1
H H13 0.9098 0.0568 0.1223 0.082 Uiso calc R 1
N N1 0.5958(4) 0.2655(2) 0.16186(7) 0.0588(5) Uani d . 1
N N2 0.7229(4) -0.0611(3) 0.26056(8) 0.0804(6) Uani d . 1
O O1 0.0884(3) 0.1719(2) 0.03293(6) 0.0754(5) Uani d . 1
O O2 0.4132(3) 0.16902(16) 0.08073(5) 0.0603(4) Uani d . 1
H H1 0.470(5) 0.312(3) 0.1835(10) 0.084(8) 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
O1 C1 O2 121.04(19) y
O1 C1 C2 130.2(2) y
O2 C1 C2 108.69(18) ?
C7 C2 C3 122.0(2) ?
C7 C2 C1 108.39(18) ?
C3 C2 C1 129.7(2) ?
C4 C3 C2 117.4(2) ?
C4 C3 H3 121.3 ?
C2 C3 H3 121.3 ?
C3 C4 C5 121.0(2) ?
C3 C4 H4 119.5 ?
C5 C4 H4 119.5 ?
C4 C5 C6 121.6(2) ?
C4 C5 H5 119.2 ?
C6 C5 H5 119.2 ?
C7 C6 C5 117.4(2) ?
C7 C6 H6 121.3 ?
C5 C6 H6 121.3 ?
C2 C7 C6 120.6(2) ?
C2 C7 C8 109.13(17) ?
C6 C7 C8 130.3(2) ?
N1 C8 O2 111.24(16) y
N1 C8 C7 113.01(16) ?
O2 C8 C7 103.13(17) ?
N1 C8 H8 109.8 ?
O2 C8 H8 109.8 ?
C7 C8 H8 109.8 ?
C13 C9 C10 116.8(2) ?
C13 C9 N1 124.44(19) ?
C10 C9 N1 118.7(2) ?
N2 C10 C9 124.3(2) ?
N2 C10 H10 117.9 ?
C9 C10 H10 117.9 ?
N2 C11 C12 123.3(2) ?
N2 C11 H11 118.3 ?
C12 C11 H11 118.3 ?
C11 C12 C13 118.8(3) ?
C11 C12 H12 120.6 ?
C13 C12 H12 120.6 ?
C9 C13 C12 119.2(2) ?
C9 C13 H13 120.4 ?
C12 C13 H13 120.4 ?
C9 N1 C8 121.75(17) ?
C9 N1 H1 115.0(15) ?
C8 N1 H1 114.6(15) ?
C11 N2 C10 117.6(2) ?
C1 O2 C8 110.65(14) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 O1 1.206(3) y
C1 O2 1.350(3) y
C1 C2 1.461(3) ?
C2 C7 1.377(3) y
C2 C3 1.382(3) ?
C3 C4 1.369(3) ?
C3 H3 0.9300 ?
C4 C5 1.381(4) ?
C4 H4 0.9300 ?
C5 C6 1.382(4) ?
C5 H5 0.9300 ?
C6 C7 1.379(3) ?
C6 H6 0.9300 ?
C7 C8 1.493(3) y
C8 N1 1.408(2) y
C8 O2 1.480(2) ?
C8 H8 0.9800 ?
C9 C13 1.374(3) ?
C9 C10 1.387(3) ?
C9 N1 1.395(3) y
C10 N2 1.322(3) ?
C10 H10 0.9300 ?
C11 N2 1.319(3) ?
C11 C12 1.358(4) ?
C11 H11 0.9300 ?
C12 C13 1.390(3) ?
C12 H12 0.9300 ?
C13 H13 0.9300 ?
N1 H1 0.98(3) ?
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 4_655 0.98(3) 2.04(3) 2.996(3) 165(2)
C5 H5 O2 1_565 0.93 2.52 3.366(3) 152.0
C13 H13 O1 1_655 0.93 2.59 3.512(3) 169.5
C4 H4 Cg1 3_465 0.93 3.345 4.075(3) 137.01
C11 H11 Cg2 4_745 0.93 2.827 3.746(3) 169.74
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 178.2(2)
O2 C1 C2 C7 0.1(2)
O1 C1 C2 C3 -2.3(4)
O2 C1 C2 C3 179.6(2)
C7 C2 C3 C4 -0.2(3)
C1 C2 C3 C4 -179.6(2)
C2 C3 C4 C5 -0.5(3)
C3 C4 C5 C6 0.5(4)
C4 C5 C6 C7 0.2(4)
C3 C2 C7 C6 0.9(3)
C1 C2 C7 C6 -179.6(2)
C3 C2 C7 C8 -179.03(19)
C1 C2 C7 C8 0.5(2)
C5 C6 C7 C2 -0.9(3)
C5 C6 C7 C8 179.0(2)
C2 C7 C8 N1 -121.1(2)
C6 C7 C8 N1 59.0(3)
C2 C7 C8 O2 -0.8(2)
C6 C7 C8 O2 179.3(2)
C13 C9 C10 N2 0.9(4)
N1 C9 C10 N2 -176.4(2)
N2 C11 C12 C13 0.2(5)
C10 C9 C13 C12 -2.1(3)
N1 C9 C13 C12 175.0(2)
C11 C12 C13 C9 1.6(4)
C13 C9 N1 C8 29.4(3)
C10 C9 N1 C8 -153.5(2)
O2 C8 N1 C9 66.5(3)
C7 C8 N1 C9 -178.02(19)
C12 C11 N2 C10 -1.4(4)
C9 C10 N2 C11 0.9(4)
O1 C1 O2 C8 -179.00(19)
C2 C1 O2 C8 -0.7(2)
N1 C8 O2 C1 122.35(19)
C7 C8 O2 C1 0.9(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21179365
