#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/17/2211702.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_2211702
loop_
_publ_author_name
'Odabaşoğlu, Mustafa'
'Büyükgüngör, Orhan'
_publ_section_title
'[2-Methyl-4-(3-oxo-1,3-dihydroisobenzofuran-1-ylamino)phenyl]isobenzofuran-1(3H)-one'
_journal_coeditor_code           AT2176
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o22
_journal_page_last               o24
_journal_paper_doi               10.1107/S1600536806051063
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C23 H17 N O4'
_chemical_formula_moiety         'C23 H17 N O4'
_chemical_formula_sum            'C23 H17 N O4'
_chemical_formula_weight         371.38
_chemical_name_systematic
;
[2-Methyl-4-(3-oxo-1,3-dihydroisobenzofuran-1-ylamino)phenyl]isobenzofuran-
1(3H)-one
;
_space_group_IT_number           7
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P -2yc'
_symmetry_space_group_name_H-M   'P 1 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                 92.444(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   5.1039(3)
_cell_length_b                   6.1761(6)
_cell_length_c                   28.5758(18)
_cell_measurement_reflns_used    7767
_cell_measurement_temperature    296
_cell_measurement_theta_max      25.02
_cell_measurement_theta_min      1.42
_cell_volume                     899.95(12)
_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 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'Stoe IPDS-2'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1019
_diffrn_reflns_av_sigmaI/netI    0.0500
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            8708
_diffrn_reflns_theta_full        25.05
_diffrn_reflns_theta_max         25.05
_diffrn_reflns_theta_min         1.43
_diffrn_standards_decay_%        <2
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  0.9899
_exptl_absorpt_correction_T_min  0.9628
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   '(X-RED32; Stoe & Cie, 2002)'
_exptl_crystal_colour            'light brown'
_exptl_crystal_density_diffrn    1.370
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             388
_exptl_crystal_size_max          0.540
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.193
_refine_ls_extinction_coef       0.055(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     258
_refine_ls_number_reflns         1592
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.085
_refine_ls_R_factor_all          0.0734
_refine_ls_R_factor_gt           0.0610
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1066P)²+0.2251P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1757
_refine_ls_wR_factor_ref         0.1845
_reflns_number_gt                1251
_reflns_number_total             1592
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            at2176.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P c'
_cod_database_code               2211702
_cod_database_fobs_code          2211702
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, -y, 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 0.2238(15) -0.0386(11) 0.3986(3) 0.0722(17) Uani d . 1
C C2 0.0468(13) 0.1036(9) 0.4237(2) 0.0616(14) Uani d . 1
C C3 -0.0572(17) 0.0779(11) 0.4675(3) 0.0764(18) Uani d . 1
H H3 -0.0166 -0.0418 0.4861 0.092 Uiso calc R 1
C C4 -0.2249(17) 0.2397(11) 0.4820(3) 0.080(2) Uani d . 1
H H4 -0.2999 0.2288 0.5110 0.096 Uiso calc R 1
C C5 -0.2815(15) 0.4182(12) 0.4534(2) 0.0738(18) Uani d . 1
H H5 -0.3926 0.5253 0.4639 0.089 Uiso calc R 1
C C6 -0.1776(13) 0.4399(11) 0.4102(2) 0.0673(16) Uani d . 1
H H6 -0.2145 0.5607 0.3916 0.081 Uiso calc R 1
C C7 -0.0174(12) 0.2778(10) 0.3952(2) 0.0606(14) Uani d . 1
C C8 0.1114(13) 0.2502(10) 0.3495(2) 0.0623(15) Uani d . 1
H H8 -0.0239 0.2272 0.3246 0.075 Uiso calc R 1
C C9 0.3990(13) 0.4331(10) 0.2953(2) 0.0620(15) Uani d . 1
C C10 0.5739(13) 0.5989(10) 0.2874(2) 0.0607(14) Uani d . 1
H H10 0.6003 0.7042 0.3104 0.073 Uiso calc R 1
C C11 0.7122(12) 0.6153(10) 0.2466(2) 0.0596(14) Uani d . 1
C C12 0.6622(12) 0.4629(10) 0.2110(2) 0.0615(15) Uani d . 1
C C13 0.4843(14) 0.2997(13) 0.2195(2) 0.0735(18) Uani d . 1
H H13 0.4482 0.1989 0.1959 0.088 Uiso calc R 1
C C14 0.3589(14) 0.2784(12) 0.2605(2) 0.0708(18) Uani d . 1
H H14 0.2479 0.1616 0.2651 0.085 Uiso calc R 1
C C15 0.9056(16) 0.7977(11) 0.2413(3) 0.081(2) Uani d . 1
H H15A 0.8393 0.8966 0.2177 0.097 Uiso calc R 1
H H15B 1.0703 0.7398 0.2321 0.097 Uiso calc R 1
H H15C 0.9301 0.8728 0.2705 0.097 Uiso calc R 1
C C16 0.7892(12) 0.4666(10) 0.1647(2) 0.0614(15) Uani d . 1
H H16 0.9132 0.5877 0.1640 0.074 Uiso calc R 1
C C17 0.6042(12) 0.4788(9) 0.1233(2) 0.0564(13) Uani d . 1
C C18 0.4134(14) 0.6369(11) 0.1111(2) 0.0677(16) Uani d . 1
H H18 0.3930 0.7595 0.1296 0.081 Uiso calc R 1
C C19 0.2579(14) 0.6036(12) 0.0709(3) 0.0724(17) Uani d . 1
H H19 0.1300 0.7048 0.0622 0.087 Uiso calc R 1
C C20 0.2904(16) 0.4215(13) 0.0435(3) 0.0796(19) Uani d . 1
H H20 0.1855 0.4044 0.0164 0.095 Uiso calc R 1
C C21 0.4750(15) 0.2636(11) 0.0555(2) 0.0726(18) Uani d . 1
H H21 0.4931 0.1401 0.0373 0.087 Uiso calc R 1
C C22 0.6318(12) 0.2983(10) 0.0958(2) 0.0614(15) Uani d . 1
C C23 0.8346(14) 0.1621(11) 0.1170(3) 0.0738(18) Uani d . 1
N N1 0.2714(11) 0.4265(9) 0.33723(18) 0.0672(14) Uani d D 1
O O1 0.3282(13) -0.2054(8) 0.4116(2) 0.0952(17) Uani d . 1
O O2 0.2655(10) 0.0486(7) 0.35637(17) 0.0762(13) Uani d . 1
O O3 0.9179(13) -0.0058(9) 0.1046(2) 0.1006(18) Uani d . 1
O O4 0.9290(9) 0.2620(8) 0.15717(18) 0.0771(13) Uani d . 1
H H1 0.315(16) 0.515(11) 0.360(2) 0.092 Uiso d 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 122.0(7) y
O1 C1 C2 129.2(7) y
O2 C1 C2 108.8(5) ?
C7 C2 C3 122.0(6) ?
C7 C2 C1 108.3(6) ?
C3 C2 C1 129.6(6) ?
C2 C3 C4 116.8(6) ?
C2 C3 H3 121.6 ?
C4 C3 H3 121.6 ?
C3 C4 C5 120.5(7) ?
C3 C4 H4 119.8 ?
C5 C4 H4 119.8 ?
C6 C5 C4 121.8(7) ?
C6 C5 H5 119.1 ?
C4 C5 H5 119.1 ?
C5 C6 C7 117.9(6) ?
C5 C6 H6 121.1 ?
C7 C6 H6 121.1 ?
C6 C7 C2 121.0(6) ?
C6 C7 C8 130.1(6) ?
C2 C7 C8 108.9(5) ?
N1 C8 O2 111.8(5) y
N1 C8 C7 114.1(5) ?
O2 C8 C7 103.3(5) ?
N1 C8 H8 109.1 ?
O2 C8 H8 109.1 ?
C7 C8 H8 109.1 ?
C10 C9 C14 118.0(6) ?
C10 C9 N1 119.5(5) ?
C14 C9 N1 122.5(6) ?
C9 C10 C11 123.0(6) ?
C9 C10 H10 118.5 ?
C11 C10 H10 118.5 ?
C10 C11 C12 118.4(6) ?
C10 C11 C15 119.8(6) ?
C12 C11 C15 121.8(6) ?
C13 C12 C11 117.6(6) ?
C13 C12 C16 118.5(6) ?
C11 C12 C16 123.9(6) ?
C14 C13 C12 123.7(6) ?
C14 C13 H13 118.2 ?
C12 C13 H13 118.2 ?
C13 C14 C9 119.3(6) ?
C13 C14 H14 120.4 ?
C9 C14 H14 120.4 ?
C11 C15 H15A 109.5 ?
C11 C15 H15B 109.5 ?
H15A C15 H15B 109.5 ?
C11 C15 H15C 109.5 ?
H15A C15 H15C 109.5 ?
H15B C15 H15C 109.5 ?
O4 C16 C17 102.9(5) ?
O4 C16 C12 110.3(5) y
C17 C16 C12 114.9(5) ?
O4 C16 H16 109.5 ?
C17 C16 H16 109.5 ?
C12 C16 H16 109.5 ?
C22 C17 C18 120.5(6) ?
C22 C17 C16 109.7(5) ?
C18 C17 C16 129.8(5) ?
C19 C18 C17 117.8(6) ?
C19 C18 H18 121.1 ?
C17 C18 H18 121.1 ?
C18 C19 C20 120.8(7) ?
C18 C19 H19 119.6 ?
C20 C19 H19 119.6 ?
C19 C20 C21 121.9(7) ?
C19 C20 H20 119.1 ?
C21 C20 H20 119.1 ?
C20 C21 C22 117.1(6) ?
C20 C21 H21 121.4 ?
C22 C21 H21 121.4 ?
C17 C22 C21 121.9(6) ?
C17 C22 C23 108.8(6) ?
C21 C22 C23 129.3(6) ?
O3 C23 O4 121.8(7) y
O3 C23 C22 130.3(8) y
O4 C23 C22 107.9(6) ?
C9 N1 C8 122.2(5) ?
C9 N1 H1 121(6) ?
C8 N1 H1 115(6) ?
C1 O2 C8 110.6(5) ?
C23 O4 C16 110.7(5) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 O1 1.210(8) y
C1 O2 1.347(8) y
C1 C2 1.468(9) ?
C2 C7 1.380(9) y
C2 C3 1.388(9) ?
C3 C4 1.391(10) ?
C3 H3 0.9300 ?
C4 C5 1.395(10) ?
C4 H4 0.9300 ?
C5 C6 1.371(9) ?
C5 H5 0.9300 ?
C6 C7 1.373(9) ?
C6 H6 0.9300 ?
C7 C8 1.498(9) ?
C8 N1 1.414(8) ?
C8 O2 1.481(8) y
C8 H8 0.9800 ?
C9 C10 1.384(9) ?
C9 C14 1.387(9) ?
C9 N1 1.389(8) y
C10 C11 1.391(9) ?
C10 H10 0.9300 ?
C11 C12 1.401(9) ?
C11 C15 1.510(9) ?
C12 C13 1.385(10) ?
C12 C16 1.499(8) y
C13 C14 1.366(9) ?
C13 H13 0.9300 ?
C14 H14 0.9300 ?
C15 H15A 0.9600 ?
C15 H15B 0.9600 ?
C15 H15C 0.9600 ?
C16 O4 1.472(8) y
C16 C17 1.483(9) ?
C16 H16 0.9800 ?
C17 C22 1.374(8) y
C17 C18 1.412(9) ?
C18 C19 1.384(10) ?
C18 H18 0.9300 ?
C19 C20 1.385(10) ?
C19 H19 0.9300 ?
C20 C21 1.388(11) ?
C20 H20 0.9300 ?
C21 C22 1.392(10) ?
C21 H21 0.9300 ?
C22 C23 1.446(10) ?
C23 O3 1.180(8) y
C23 O4 1.372(10) y
N1 H1 0.88(7) ?
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 1_565 0.88(7) 2.26(6) 3.118(7) 164(7)
C5 H5 O1 1_465 0.93 2.62 3.256(9) 126.3
C19 H19 O3 1_465 0.93 2.44 3.147(9) 132.9
C15 H15b Cg1 1_655 0.96 3.00 3.861(8) 149.63
C4 H4 Cg2 2_465 0.93 3.18 3.912(9) 136.8
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
O1 C1 C2 C7 178.5(8) ?
O2 C1 C2 C7 0.3(8) ?
O1 C1 C2 C3 -3.9(13) ?
O2 C1 C2 C3 177.9(7) ?
C7 C2 C3 C4 -1.7(11) ?
C1 C2 C3 C4 -179.0(7) ?
C2 C3 C4 C5 -0.3(11) ?
C3 C4 C5 C6 0.7(12) ?
C4 C5 C6 C7 1.0(11) ?
C5 C6 C7 C2 -3.0(10) ?
C5 C6 C7 C8 176.4(7) ?
C3 C2 C7 C6 3.4(10) ?
C1 C2 C7 C6 -178.8(6) ?
C3 C2 C7 C8 -176.1(7) ?
C1 C2 C7 C8 1.7(7) ?
C6 C7 C8 N1 56.1(9) y
C2 C7 C8 N1 -124.5(6) ?
C6 C7 C8 O2 177.6(7) ?
C2 C7 C8 O2 -2.9(6) ?
C14 C9 C10 C11 -0.8(9) ?
N1 C9 C10 C11 179.1(6) ?
C9 C10 C11 C12 3.2(9) ?
C9 C10 C11 C15 -178.2(6) ?
C10 C11 C12 C13 -2.4(9) ?
C15 C11 C12 C13 179.1(7) ?
C10 C11 C12 C16 177.6(6) ?
C15 C11 C12 C16 -1.0(10) ?
C11 C12 C13 C14 -0.8(11) ?
C16 C12 C13 C14 179.2(7) ?
C12 C13 C14 C9 3.3(12) ?
C10 C9 C14 C13 -2.5(10) ?
N1 C9 C14 C13 177.7(7) ?
C13 C12 C16 O4 -57.8(8) ?
C11 C12 C16 O4 122.2(7) ?
C13 C12 C16 C17 57.8(8) ?
C11 C12 C16 C17 -122.1(6) y
O4 C16 C17 C22 1.2(6) ?
C12 C16 C17 C22 -118.6(6) ?
O4 C16 C17 C18 178.7(6) ?
C12 C16 C17 C18 58.9(9) ?
C22 C17 C18 C19 -0.1(9) ?
C16 C17 C18 C19 -177.4(6) ?
C17 C18 C19 C20 -0.4(10) ?
C18 C19 C20 C21 1.2(11) ?
C19 C20 C21 C22 -1.5(11) ?
C18 C17 C22 C21 -0.1(9) ?
C16 C17 C22 C21 177.6(6) ?
C18 C17 C22 C23 -178.5(6) ?
C16 C17 C22 C23 -0.7(7) ?
C20 C21 C22 C17 0.9(10) ?
C20 C21 C22 C23 178.9(7) ?
C17 C22 C23 O3 -180.0(7) ?
C21 C22 C23 O3 1.9(12) ?
C17 C22 C23 O4 -0.2(7) ?
C21 C22 C23 O4 -178.3(7) ?
C10 C9 N1 C8 -173.4(6) y
C14 C9 N1 C8 6.5(10) ?
O2 C8 N1 C9 65.6(8) ?
C7 C8 N1 C9 -177.6(6) ?
O1 C1 O2 C8 179.4(7) ?
C2 C1 O2 C8 -2.2(7) ?
N1 C8 O2 C1 126.3(6) ?
C7 C8 O2 C1 3.2(7) ?
O3 C23 O4 C16 -179.2(6) ?
C22 C23 O4 C16 1.0(7) ?
C17 C16 O4 C23 -1.4(6) ?
C12 C16 O4 C23 121.6(6) ?
