#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/93/2209319.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_2209319
loop_
_publ_author_name
'Odabaşoğlu, Mustafa'
'Büyükgüngör, Orhan'
_publ_section_title
;
 3-(4-Methylpyridin-2-ylamino)isobenzofuran-1(3H)-one
;
_journal_coeditor_code           SJ2066
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2316
_journal_page_last               o2317
_journal_paper_doi               10.1107/S160053680601717X
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C14 H12 N2 O2'
_chemical_formula_moiety         'C14 H12 N2 O2'
_chemical_formula_sum            'C14 H12 N2 O2'
_chemical_formula_weight         240.26
_chemical_name_common            3-(4-methyl-3-pyridylamino)phthalide
_chemical_name_systematic
;
3-(4-methylpyridin-2-ylamino)isobenzofuran-1(3H)-one
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                87.387(17)
_cell_angle_beta                 78.177(18)
_cell_angle_gamma                78.456(18)
_cell_formula_units_Z            2
_cell_length_a                   7.6621(18)
_cell_length_b                   8.0381(18)
_cell_length_c                   10.616(2)
_cell_measurement_reflns_used    5736
_cell_measurement_temperature    296
_cell_measurement_theta_max      27.04
_cell_measurement_theta_min      3.24
_cell_volume                     627.0(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  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_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  0.0791
_diffrn_reflns_av_sigmaI/netI    0.0689
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5736
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         3.40
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.9868
_exptl_absorpt_correction_T_min  0.9601
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   '(X-RED32; Stoe & Cie, 2002)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.273
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             252
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.516
_refine_diff_density_min         -0.311
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2454
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.090
_refine_ls_R_factor_all          0.1235
_refine_ls_R_factor_gt           0.0795
_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)+(0.0967P)²+0.443P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2010
_refine_ls_wR_factor_ref         0.2371
_reflns_number_gt                1575
_reflns_number_total             2454
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sj2066.cif
_cod_data_source_block           I
_cod_original_sg_symbol_Hall     -P1
_cod_database_code               2209319
_cod_database_fobs_code          2209319
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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 0.6909(5) 0.5300(5) 0.0678(4) 0.0489(9) Uani d . 1
C C2 0.6668(5) 0.7127(4) 0.0968(3) 0.0451(8) Uani d . 1
C C3 0.7730(6) 0.8298(5) 0.0444(4) 0.0605(10) Uani d . 1
H H3 0.8784 0.7984 -0.0176 0.073 Uiso calc R 1
C C4 0.7152(7) 0.9957(5) 0.0886(5) 0.0688(12) Uani d . 1
H H4 0.7825 1.0775 0.0548 0.083 Uiso calc R 1
C C5 0.5609(7) 1.0411(5) 0.1809(5) 0.0679(12) Uani d . 1
H H5 0.5263 1.1531 0.2087 0.081 Uiso calc R 1
C C6 0.4552(6) 0.9249(5) 0.2341(4) 0.0591(10) Uani d . 1
H H6 0.3510 0.9566 0.2971 0.071 Uiso calc R 1
C C7 0.5108(5) 0.7583(4) 0.1895(4) 0.0488(9) Uani d . 1
C C8 0.4177(6) 0.6076(4) 0.2213(4) 0.0546(9) Uani d . 1
H H8 0.3015 0.6307 0.1925 0.066 Uiso calc R 1
C C9 0.2854(5) 0.4378(5) 0.4009(4) 0.0515(9) Uani d . 1
C C13 0.2078(7) 0.2619(5) 0.5666(4) 0.0646(11) Uani d . 1
H H13 0.2263 0.2132 0.6451 0.077 Uiso calc R 1
C C12 0.0748(6) 0.2148(5) 0.5136(4) 0.0563(10) Uani d . 1
H H12 0.0061 0.1388 0.5567 0.068 Uiso calc R 1
C C11 0.0446(6) 0.2820(4) 0.3951(4) 0.0525(9) Uani d . 1
C C10 0.1567(6) 0.3947(5) 0.3365(4) 0.0572(10) Uani d . 1
H H10 0.1459 0.4405 0.2558 0.069 Uiso calc R 1
C C14 -0.0984(8) 0.2351(6) 0.3326(5) 0.0767(14) Uani d . 1
H H14A -0.1319 0.3219 0.2719 0.115 Uiso calc R 1
H H14C -0.2034 0.2248 0.3973 0.115 Uiso calc R 1
H H14B -0.0509 0.1289 0.2886 0.115 Uiso calc R 1
N N1 0.3887(5) 0.5609(4) 0.3519(3) 0.0600(9) Uani d . 1
H H1 0.4358 0.6093 0.4036 0.072 Uiso calc R 1
N N2 0.3127(5) 0.3727(4) 0.5136(3) 0.0582(9) Uani d . 1
O O1 0.8086(4) 0.4395(4) -0.0065(3) 0.0637(8) Uani d . 1
O O2 0.5472(4) 0.4701(3) 0.1407(3) 0.0588(8) 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
_geom_angle_publ_flag
O1 C1 O2 121.5(3) y
O1 C1 C2 130.5(4) y
O2 C1 C2 107.9(3) ?
C7 C2 C3 121.6(3) ?
C7 C2 C1 108.7(3) ?
C3 C2 C1 129.6(4) ?
C4 C3 C2 117.2(4) ?
C4 C3 H3 121.4 ?
C2 C3 H3 121.4 ?
C5 C4 C3 121.2(4) ?
C5 C4 H4 119.4 ?
C3 C4 H4 119.4 ?
C4 C5 C6 121.8(4) ?
C4 C5 H5 119.1 ?
C6 C5 H5 119.1 ?
C5 C6 C7 117.4(4) ?
C5 C6 H6 121.3 ?
C7 C6 H6 121.3 ?
C2 C7 C6 120.6(3) ?
C2 C7 C8 109.6(3) ?
C6 C7 C8 129.7(4) ?
N1 C8 O2 111.0(3) y
N1 C8 C7 114.7(3) ?
O2 C8 C7 102.3(3) ?
N1 C8 H8 109.6 ?
O2 C8 H8 109.6 ?
C7 C8 H8 109.6 ?
N2 C9 N1 114.7(3) ?
N2 C9 C10 123.4(3) ?
N1 C9 C10 121.8(3) ?
N2 C13 C12 125.2(4) ?
N2 C13 H13 117.4 ?
C12 C13 H13 117.4 ?
C13 C12 C11 119.4(4) ?
C13 C12 H12 120.3 ?
C11 C12 H12 120.3 ?
C12 C11 C10 116.2(3) ?
C12 C11 C14 121.8(4) ?
C10 C11 C14 122.0(4) ?
C11 C10 C9 119.7(3) ?
C11 C10 H10 120.1 ?
C9 C10 H10 120.1 ?
C11 C14 H14A 109.5 ?
C11 C14 H14C 109.5 ?
H14A C14 H14C 109.5 ?
C11 C14 H14B 109.5 ?
H14A C14 H14B 109.5 ?
H14C C14 H14B 109.5 ?
C8 N1 C9 122.2(3) ?
C8 N1 H1 118.9 ?
C9 N1 H1 118.9 ?
C9 N2 C13 116.1(3) ?
C1 O2 C8 111.3(3) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 O1 1.209(5) y
C1 O2 1.369(5) y
C1 C2 1.481(5) ?
C2 C7 1.381(5) y
C2 C3 1.390(5) ?
C3 C4 1.389(6) ?
C3 H3 0.9300 ?
C4 C5 1.370(7) ?
C4 H4 0.9300 ?
C5 C6 1.384(6) ?
C5 H5 0.9300 ?
C6 C7 1.395(5) ?
C6 H6 0.9300 ?
C7 C8 1.517(5) y
C8 N1 1.403(5) y
C8 O2 1.496(5) ?
C8 H8 0.9800 ?
C9 N2 1.323(5) ?
C9 N1 1.406(5) y
C9 C10 1.412(5) ?
C13 N2 1.346(5) ?
C13 C12 1.381(6) ?
C13 H13 0.9300 ?
C12 C11 1.390(5) ?
C12 H12 0.9300 ?
C11 C10 1.409(5) ?
C11 C14 1.507(6) ?
C10 H10 0.9300 ?
C14 H14A 0.9600 ?
C14 H14C 0.9600 ?
C14 H14B 0.9600 ?
N1 H1 0.8600 ?
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 2_666 0.86 2.31 3.075(5) 148.7
C8 H8 O1 2_665 0.98 2.43 3.211(6) 136
C6 H6 Cg1 1_565 0.93 3.373 4.039(4) 130.46
C13 H13 Cg2 2_666 0.93 2.815 3.702(5) 159.95
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 -179.9(4)
O2 C1 C2 C7 1.6(4)
O1 C1 C2 C3 0.9(6)
O2 C1 C2 C3 -177.7(4)
C7 C2 C3 C4 -0.4(6)
C1 C2 C3 C4 178.8(4)
C2 C3 C4 C5 0.7(6)
C3 C4 C5 C6 -0.3(7)
C4 C5 C6 C7 -0.4(7)
C3 C2 C7 C6 -0.3(5)
C1 C2 C7 C6 -179.6(3)
C3 C2 C7 C8 176.3(3)
C1 C2 C7 C8 -3.1(4)
C5 C6 C7 C2 0.7(6)
C5 C6 C7 C8 -175.1(4)
C2 C7 C8 N1 123.5(4)
C6 C7 C8 N1 -60.4(6)
C2 C7 C8 O2 3.3(4)
C6 C7 C8 O2 179.4(4)
N2 C13 C12 C11 1.2(7)
C13 C12 C11 C10 0.6(6)
C13 C12 C11 C14 179.9(4)
C12 C11 C10 C9 -2.3(6)
C14 C11 C10 C9 178.4(4)
N2 C9 C10 C11 2.5(6)
N1 C9 C10 C11 -174.2(4)
O2 C8 N1 C9 -72.5(5)
C7 C8 N1 C9 172.2(4)
N2 C9 N1 C8 161.4(4)
C10 C9 N1 C8 -21.6(6)
N1 C9 N2 C13 176.2(4)
C10 C9 N2 C13 -0.8(6)
C12 C13 N2 C9 -1.1(6)
O1 C1 O2 C8 -178.1(3)
C2 C1 O2 C8 0.6(4)
N1 C8 O2 C1 -125.1(3)
C7 C8 O2 C1 -2.3(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 2404907
