#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/93/2209323.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_2209323
loop_
_publ_author_name
'Odabaşoğlu, Mustafa'
'Büyükgüngör, Orhan'
_publ_section_title
;
 3-(4-Ethoxyanilino)isobenzofuran-1(3H)-one
;
_journal_coeditor_code           SJ2076
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2558
_journal_page_last               o2559
_journal_paper_doi               10.1107/S1600536806019350
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C16 H15 N O3'
_chemical_formula_moiety         'C16 H15 N O3'
_chemical_formula_sum            'C16 H15 N O3'
_chemical_formula_weight         269.29
_chemical_name_common            3-(4-ethoxyanilino)phthalide
_chemical_name_systematic
;
3-(4-ethoxyanilino)isobenzofuran-1(3H)-one
;
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_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            4
_cell_length_a                   8.6851(11)
_cell_length_b                   28.485(3)
_cell_length_c                   5.4644(5)
_cell_measurement_reflns_used    8038
_cell_measurement_temperature    296
_cell_measurement_theta_max      25.98
_cell_measurement_theta_min      1.43
_cell_volume                     1351.9(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  '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 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Stoe IPDS-2'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_source
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1355
_diffrn_reflns_av_sigmaI/netI    0.0718
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            11317
_diffrn_reflns_theta_full        26.01
_diffrn_reflns_theta_max         26.01
_diffrn_reflns_theta_min         1.43
_diffrn_standards_decay_%        <2
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.9959
_exptl_absorpt_correction_T_min  0.9737
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   '(X-RED32; Stoe & Cie, 2002)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.115
_refine_diff_density_min         -0.134
_refine_ls_extinction_coef       0.031(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   0.954
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         1478
_refine_ls_number_restraints     15
_refine_ls_restrained_S_all      0.949
_refine_ls_R_factor_all          0.0805
_refine_ls_R_factor_gt           0.0404
_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)+(0.0302P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0716
_refine_ls_wR_factor_ref         0.0823
_reflns_number_gt                915
_reflns_number_total             1478
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sj2076.cif
_cod_data_source_block           I
_cod_original_cell_volume        1351.8(2)
_cod_database_code               2209323
_cod_database_fobs_code          2209323
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y+1/2, z+1/2'
'x+1/2, -y+1/2, 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 0.5350(4) 0.32900(12) 0.1474(6) 0.0575(8) Uani d . 1
C C2 0.4235(4) 0.30886(11) 0.3209(6) 0.0526(8) Uani d . 1
C C3 0.3619(4) 0.26445(13) 0.3361(8) 0.0686(10) Uani d . 1
H H3 0.3863 0.2416 0.2206 0.082 Uiso calc R 1
C C4 0.2644(5) 0.25474(14) 0.5242(8) 0.0741(11) Uani d . 1
H H4 0.2242 0.2246 0.5397 0.089 Uiso calc R 1
C C5 0.2244(4) 0.28838(14) 0.6908(7) 0.0714(11) Uani d . 1
H H5 0.1556 0.2808 0.8150 0.086 Uiso calc R 1
C C6 0.2843(4) 0.33399(12) 0.6797(6) 0.0632(9) Uani d . 1
H H6 0.2579 0.3568 0.7942 0.076 Uiso calc R 1
C C7 0.3856(4) 0.34345(10) 0.4881(5) 0.0493(8) Uani d . 1
C C8 0.4715(4) 0.38747(11) 0.4302(6) 0.0508(8) Uani d . 1
H H8 0.3983 0.4124 0.3880 0.061 Uiso calc R 1
C C9 0.6468(4) 0.44524(10) 0.6152(6) 0.0470(7) Uani d . 1
C C10 0.7495(4) 0.45576(11) 0.8015(6) 0.0545(8) Uani d . 1
H H10 0.7672 0.4337 0.9238 0.065 Uiso calc R 1
C C11 0.8263(4) 0.49830(12) 0.8098(6) 0.0558(8) Uani d . 1
H H11 0.8943 0.5046 0.9371 0.067 Uiso calc R 1
C C12 0.8019(4) 0.53138(11) 0.6282(6) 0.0505(8) Uani d U 1
C C13 0.7017(4) 0.52114(12) 0.4425(6) 0.0543(8) Uani d . 1
H H13 0.6845 0.5434 0.3210 0.065 Uiso calc R 1
C C14 0.6254(4) 0.47863(11) 0.4304(6) 0.0526(8) Uani d . 1
H H14 0.5600 0.4722 0.2998 0.063 Uiso calc R 1
C C15 0.9759(4) 0.58774(13) 0.8094(8) 0.0677(9) Uani d U 1
H H15A 1.0620 0.5660 0.8113 0.081 Uiso calc R 1
H H15B 0.9255 0.5865 0.9677 0.081 Uiso calc R 1
C C16 1.0313(5) 0.63623(13) 0.7590(8) 0.0867(13) Uani d . 1
H H16A 0.9453 0.6574 0.7565 0.104 Uiso calc R 1
H H16B 1.0824 0.6370 0.6033 0.104 Uiso calc R 1
H H16C 1.1020 0.6456 0.8849 0.104 Uiso calc R 1
N N1 0.5667(3) 0.40276(8) 0.6211(4) 0.0542(7) Uani d . 1
H H1 0.5763 0.3851 0.7480 0.065 Uiso calc R 1
O O1 0.5999(3) 0.31108(9) -0.0249(4) 0.0761(8) Uani d . 1
O O2 0.5623(3) 0.37423(7) 0.2080(4) 0.0571(6) Uani d . 1
O O3 0.8694(3) 0.57509(8) 0.6196(4) 0.0643(7) Uani d U 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 120.8(3) y
O1 C1 C2 130.0(3) y
O2 C1 C2 109.2(3) ?
C3 C2 C7 121.5(3) ?
C3 C2 C1 130.8(3) ?
C7 C2 C1 107.7(3) ?
C4 C3 C2 118.3(4) ?
C4 C3 H3 120.8 ?
C2 C3 H3 120.8 ?
C3 C4 C5 121.3(4) ?
C3 C4 H4 119.4 ?
C5 C4 H4 119.4 ?
C4 C5 C6 121.8(4) ?
C4 C5 H5 119.1 ?
C6 C5 H5 119.1 ?
C7 C6 C5 116.5(3) ?
C7 C6 H6 121.8 ?
C5 C6 H6 121.8 ?
C2 C7 C6 120.6(3) ?
C2 C7 C8 109.9(3) ?
C6 C7 C8 129.6(3) ?
N1 C8 C7 113.5(3) ?
N1 C8 O2 111.8(2) y
C7 C8 O2 102.9(2) ?
N1 C8 H8 109.5 ?
C7 C8 H8 109.5 ?
O2 C8 H8 109.5 ?
C10 C9 N1 119.4(3) ?
C10 C9 C14 117.9(3) ?
N1 C9 C14 122.6(3) ?
C11 C10 C9 121.6(3) ?
C11 C10 H10 119.2 ?
C9 C10 H10 119.2 ?
C10 C11 C12 119.9(3) ?
C10 C11 H11 120.1 ?
C12 C11 H11 120.1 ?
C13 C12 O3 116.0(3) ?
C13 C12 C11 118.9(3) ?
O3 C12 C11 125.1(3) ?
C12 C13 C14 121.8(3) ?
C12 C13 H13 119.1 ?
C14 C13 H13 119.1 ?
C13 C14 C9 119.8(3) ?
C13 C14 H14 120.1 ?
C9 C14 H14 120.1 ?
O3 C15 C16 107.9(3) ?
O3 C15 H15A 110.1 ?
C16 C15 H15A 110.1 ?
O3 C15 H15B 110.1 ?
C16 C15 H15B 110.1 ?
H15A C15 H15B 108.4 ?
C15 C16 H16A 109.5 ?
C15 C16 H16B 109.5 ?
H16A C16 H16B 109.5 ?
C15 C16 H16C 109.5 ?
H16A C16 H16C 109.5 ?
H16B C16 H16C 109.5 ?
C9 N1 C8 123.1(3) ?
C9 N1 H1 118.4 ?
C8 N1 H1 118.4 ?
C1 O2 C8 110.3(2) ?
C12 O3 C15 118.5(3) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 O1 1.210(4) y
C1 O2 1.351(4) y
C1 C2 1.472(4) ?
C2 C3 1.376(5) ?
C2 C7 1.383(4) y
C3 C4 1.360(5) ?
C3 H3 0.9300 ?
C4 C5 1.367(5) ?
C4 H4 0.9300 ?
C5 C6 1.401(5) ?
C5 H5 0.9300 ?
C6 C7 1.394(4) ?
C6 H6 0.9300 ?
C7 C8 1.493(4) ?
C8 N1 1.400(4) y
C8 O2 1.496(4) ?
C8 H8 0.9800 ?
C9 C10 1.386(4) ?
C9 N1 1.396(4) y
C9 C14 1.400(4) ?
C10 C11 1.384(4) ?
C10 H10 0.9300 ?
C11 C12 1.385(4) ?
C11 H11 0.9300 ?
C12 C13 1.368(4) ?
C12 O3 1.377(4) ?
C13 C14 1.382(4) ?
C13 H13 0.9300 ?
C14 H14 0.9300 ?
C15 O3 1.436(4) ?
C15 C16 1.488(5) ?
C15 H15A 0.9700 ?
C15 H15B 0.9700 ?
C16 H16A 0.9600 ?
C16 H16B 0.9600 ?
C16 H16C 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 O1 1_556 0.86 2.46 3.263(3) 156.4
N1 H1 O2 1_556 0.86 2.54 3.309(3) 150.0
C14 H14 Cg2 2_554 0.93 2.8891 3.607(4) 134.95
C15 H15A Cg2 2_655 0.97 2.9478 3.788(4) 145.52
C16 H16A Cg1 2_555 0.96 2.9805 3.842(4) 149.99
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 C3 0.0(6)
O2 C1 C2 C3 -179.2(3)
O1 C1 C2 C7 178.8(3)
O2 C1 C2 C7 -0.3(3)
C7 C2 C3 C4 -1.5(5)
C1 C2 C3 C4 177.3(3)
C2 C3 C4 C5 1.9(6)
C3 C4 C5 C6 -1.5(6)
C4 C5 C6 C7 0.7(5)
C3 C2 C7 C6 0.7(5)
C1 C2 C7 C6 -178.3(3)
C3 C2 C7 C8 178.8(3)
C1 C2 C7 C8 -0.2(3)
C5 C6 C7 C2 -0.3(5)
C5 C6 C7 C8 -178.0(3)
C2 C7 C8 N1 -120.5(3)
C6 C7 C8 N1 57.4(4)
C2 C7 C8 O2 0.6(3)
C6 C7 C8 O2 178.5(3)
N1 C9 C10 C11 -177.0(3)
C14 C9 C10 C11 1.6(5)
C9 C10 C11 C12 -0.4(5)
C10 C11 C12 C13 -0.2(5)
C10 C11 C12 O3 178.8(3)
O3 C12 C13 C14 -179.5(3)
C11 C12 C13 C14 -0.5(5)
C12 C13 C14 C9 1.7(5)
C10 C9 C14 C13 -2.2(5)
N1 C9 C14 C13 176.3(3)
C10 C9 N1 C8 -174.1(3)
C14 C9 N1 C8 7.4(5)
C7 C8 N1 C9 -174.1(3)
O2 C8 N1 C9 70.0(4)
O1 C1 O2 C8 -178.5(3)
C2 C1 O2 C8 0.7(3)
N1 C8 O2 C1 121.4(3)
C7 C8 O2 C1 -0.8(3)
C13 C12 O3 C15 -179.8(3)
C11 C12 O3 C15 1.2(5)
C16 C15 O3 C12 -179.7(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 2404885
