#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:58:33 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202018 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/22/8102213.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_8102213
loop_
_publ_author_name
'Junyan Wang'
'Dave M. Johnson'
'Edward R. T. Tiekink'
_publ_section_title
;
 Crystal structure of
 2-((3-oxo-1,3-dihydro-2-benzofuran-5-yl)methyl)-1H-isoindole-1,3(2H)-dione,
 C17H11NO4, a triclinic polymorph
;
_journal_issue                   1
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              29
_journal_volume                  223
_journal_year                    2008
_chemical_formula_moiety         'C17 H11 N O4'
_chemical_formula_structural     'C17 H11 N O4'
_chemical_formula_sum            'C17 H11 N O4'
_chemical_formula_weight         293.27
_chemical_name_systematic
;
2-((3-oxo-1,3-dihydro-2-benzofuran-5-yl)methyl)-1H-isoindole-1,3(2H)-dione
;
_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_date             2007-05-31
_audit_creation_method           SHELXL-97
_cell_angle_alpha                96.183(8)
_cell_angle_beta                 104.654(7)
_cell_angle_gamma                109.326(7)
_cell_formula_units_Z            2
_cell_length_a                   6.9911(10)
_cell_length_b                   8.4863(11)
_cell_length_c                   11.8735(15)
_cell_measurement_reflns_used    4812
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      29.5
_cell_measurement_theta_min      2.6
_cell_volume                     628.82(15)
_computing_cell_refinement       CrystalClear
_computing_data_collection       'CrystalClear (Rigaku, 2005)'
_computing_data_reduction        CrystalClear
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR-92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      153(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Rigaku AFC12 & SATURN724'
_diffrn_measurement_method       omega
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.017
_diffrn_reflns_av_sigmaI/netI    0.016
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4067
_diffrn_reflns_theta_full        26.5
_diffrn_reflns_theta_max         26.49
_diffrn_reflns_theta_min         2.60
_diffrn_standards_decay_%        '< 1'
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.663
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Higashi, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.549
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             304
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.25
_refine_diff_density_min         -0.19
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.17
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2576
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.17
_refine_ls_R_factor_all          0.048
_refine_ls_R_factor_gt           0.045
_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)+(0.0360P)²+0.4236P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.105
_refine_ls_wR_factor_ref         0.107
_reflns_number_gt                2439
_reflns_number_total             2576
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            1267-2142.cff
_cod_data_source_block           global
_cod_database_code               8102213
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_Wyckoff_symbol
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.2674(2) 0.30147(15) 0.49093(11) 0.0262(3) Uani 1 2 i d . . .
O2 O 0.0066(2) -0.15792(15) 0.18381(10) 0.0275(3) Uani 1 2 i d . . .
O3 O 0.7232(2) 0.31049(16) -0.03625(11) 0.0283(3) Uani 1 2 i d . . .
O4 O 0.4395(2) 0.06880(16) -0.11558(11) 0.0304(3) Uani 1 2 i d . . .
N1 N 0.1282(2) 0.09687(17) 0.31779(12) 0.0197(3) Uani 1 2 i d . . .
C1 C 0.2194(2) 0.1570(2) 0.43986(14) 0.0191(3) Uani 1 2 i d . . .
C2 C 0.2401(2) 0.0083(2) 0.48934(14) 0.0189(3) Uani 1 2 i d . . .
C3 C 0.3205(3) -0.0046(2) 0.60439(15) 0.0219(3) Uani 1 2 i d . . .
H3 H 0.3738 0.0911 0.6686 0.026 Uiso 1 2 i calc R . .
C4 C 0.3211(3) -0.1629(2) 0.62342(15) 0.0243(4) Uani 1 2 i d . . .
H4 H 0.3753 -0.1760 0.7023 0.029 Uiso 1 2 i calc R . .
C5 C 0.2442(3) -0.3025(2) 0.52968(16) 0.0253(4) Uani 1 2 i d . . .
H5 H 0.2474 -0.4093 0.5451 0.030 Uiso 1 2 i calc R . .
C6 C 0.1625(3) -0.2879(2) 0.41369(16) 0.0239(4) Uani 1 2 i d . . .
H6 H 0.1088 -0.3831 0.3491 0.029 Uiso 1 2 i calc R . .
C7 C 0.1619(2) -0.1309(2) 0.39560(14) 0.0193(3) Uani 1 2 i d . . .
C8 C 0.0876(2) -0.0755(2) 0.28412(14) 0.0195(3) Uani 1 2 i d . . .
C9 C 0.0815(3) 0.2028(2) 0.23436(14) 0.0206(3) Uani 1 2 i d . . .
H9A H 0.0491 0.2950 0.2743 0.025 Uiso 1 2 i calc R . .
H9B H -0.0457 0.1325 0.1664 0.025 Uiso 1 2 i calc R . .
C10 C 0.2673(3) 0.2804(2) 0.18906(14) 0.0190(3) Uani 1 2 i d . . .
C11 C 0.2905(3) 0.1902(2) 0.09251(14) 0.0206(3) Uani 1 2 i d . . .
H11 H 0.1865 0.0813 0.0509 0.025 Uiso 1 2 i calc R . .
C12 C 0.4694(3) 0.2634(2) 0.05847(14) 0.0204(3) Uani 1 2 i d . . .
C13 C 0.5310(3) 0.1966(2) -0.04011(14) 0.0223(3) Uani 1 2 i d . . .
C14 C 0.7936(3) 0.4579(2) 0.05835(15) 0.0251(4) Uani 1 2 i d . . .
H14A H 0.8078 0.5626 0.0261 0.030 Uiso 1 2 i calc R . .
H14B H 0.9324 0.4733 0.1151 0.030 Uiso 1 2 i calc R . .
C15 C 0.6229(3) 0.4199(2) 0.11741(14) 0.0209(3) Uani 1 2 i d . . .
C16 C 0.6011(3) 0.5117(2) 0.21374(15) 0.0227(3) Uani 1 2 i d . . .
H16 H 0.7057 0.6207 0.2548 0.027 Uiso 1 2 i calc R . .
C17 C 0.4225(3) 0.4401(2) 0.24835(14) 0.0216(3) Uani 1 2 i d . . .
H17 H 0.4049 0.5013 0.3143 0.026 Uiso 1 2 i calc R . .
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C13 O3 C14 110.87(12) . . ?
C1 N1 C8 112.33(13) . . ?
C1 N1 C9 123.90(13) . . ?
C8 N1 C9 123.76(13) . . ?
O1 C1 N1 124.97(15) . . ?
O1 C1 C2 129.25(15) . . ?
N1 C1 C2 105.78(13) . . ?
C3 C2 C7 121.50(15) . . ?
C3 C2 C1 130.58(15) . . ?
C7 C2 C1 107.92(14) . . ?
C2 C3 C4 117.39(15) . . ?
C2 C3 H3 121.3 . . ?
C4 C3 H3 121.3 . . ?
C5 C4 C3 121.31(16) . . ?
C5 C4 H4 119.3 . . ?
C3 C4 H4 119.3 . . ?
C4 C5 C6 120.73(16) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C7 C6 C5 117.62(16) . . ?
C7 C6 H6 121.2 . . ?
C5 C6 H6 121.2 . . ?
C6 C7 C2 121.44(16) . . ?
C6 C7 C8 130.24(15) . . ?
C2 C7 C8 108.31(14) . . ?
O2 C8 N1 125.14(15) . . ?
O2 C8 C7 129.20(15) . . ?
N1 C8 C7 105.66(13) . . ?
N1 C9 C10 111.07(13) . . ?
N1 C9 H9A 109.4 . . ?
C10 C9 H9A 109.4 . . ?
N1 C9 H9B 109.4 . . ?
C10 C9 H9B 109.4 . . ?
H9A C9 H9B 108.0 . . ?
C17 C10 C11 119.70(15) . . ?
C17 C10 C9 119.92(14) . . ?
C11 C10 C9 120.30(14) . . ?
C12 C11 C10 117.98(15) . . ?
C12 C11 H11 121.0 . . ?
C10 C11 H11 121.0 . . ?
C15 C12 C11 122.32(15) . . ?
C15 C12 C13 108.70(15) . . ?
C11 C12 C13 128.97(15) . . ?
O4 C13 O3 121.63(15) . . ?
O4 C13 C12 130.52(16) . . ?
O3 C13 C12 107.85(14) . . ?
O3 C14 C15 104.49(13) . . ?
O3 C14 H14A 110.9 . . ?
C15 C14 H14A 110.9 . . ?
O3 C14 H14B 110.9 . . ?
C15 C14 H14B 110.9 . . ?
H14A C14 H14B 108.9 . . ?
C12 C15 C16 120.25(15) . . ?
C12 C15 C14 108.04(14) . . ?
C16 C15 C14 131.71(15) . . ?
C15 C16 C17 117.93(15) . . ?
C15 C16 H16 121.0 . . ?
C17 C16 H16 121.0 . . ?
C10 C17 C16 121.80(15) . . ?
C10 C17 H17 119.1 . . ?
C16 C17 H17 119.1 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.2036(19) . ?
O2 C8 1.202(2) . ?
O3 C13 1.357(2) . ?
O3 C14 1.442(2) . ?
O4 C13 1.196(2) . ?
N1 C1 1.388(2) . ?
N1 C8 1.386(2) . ?
N1 C9 1.455(2) . ?
C1 C2 1.482(2) . ?
C2 C3 1.371(2) . ?
C2 C7 1.384(2) . ?
C3 C4 1.387(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.386(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.387(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.373(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.480(2) . ?
C9 C10 1.508(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C17 1.394(2) . ?
C10 C11 1.383(2) . ?
C11 C12 1.382(2) . ?
C11 H11 0.9500 . ?
C12 C15 1.372(2) . ?
C12 C13 1.466(2) . ?
C14 C15 1.496(2) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.384(2) . ?
C16 C17 1.382(2) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8 N1 C1 O1 -179.22(15) . . . . ?
C9 N1 C1 O1 1.1(2) . . . . ?
C8 N1 C1 C2 0.25(17) . . . . ?
C9 N1 C1 C2 -179.40(13) . . . . ?
O1 C1 C2 C3 -0.9(3) . . . . ?
N1 C1 C2 C3 179.64(16) . . . . ?
O1 C1 C2 C7 179.59(16) . . . . ?
N1 C1 C2 C7 0.15(17) . . . . ?
C7 C2 C3 C4 0.2(2) . . . . ?
C1 C2 C3 C4 -179.26(15) . . . . ?
C2 C3 C4 C5 0.3(2) . . . . ?
C3 C4 C5 C6 -0.5(3) . . . . ?
C4 C5 C6 C7 0.3(3) . . . . ?
C5 C6 C7 C2 0.1(2) . . . . ?
C5 C6 C7 C8 179.66(16) . . . . ?
C3 C2 C7 C6 -0.4(2) . . . . ?
C1 C2 C7 C6 179.18(14) . . . . ?
C3 C2 C7 C8 179.99(14) . . . . ?
C1 C2 C7 C8 -0.46(17) . . . . ?
C1 N1 C8 O2 178.90(15) . . . . ?
C9 N1 C8 O2 -1.4(2) . . . . ?
C1 N1 C8 C7 -0.52(17) . . . . ?
C9 N1 C8 C7 179.14(13) . . . . ?
C6 C7 C8 O2 1.6(3) . . . . ?
C2 C7 C8 O2 -178.79(16) . . . . ?
C6 C7 C8 N1 -178.99(16) . . . . ?
C2 C7 C8 N1 0.60(17) . . . . ?
C1 N1 C9 C10 90.60(18) . . . . ?
C8 N1 C9 C10 -89.01(18) . . . . ?
N1 C9 C10 C17 -91.16(18) . . . . ?
N1 C9 C10 C11 85.55(18) . . . . ?
C17 C10 C11 C12 0.1(2) . . . . ?
C9 C10 C11 C12 -176.66(14) . . . . ?
C10 C11 C12 C15 0.5(2) . . . . ?
C10 C11 C12 C13 -179.39(15) . . . . ?
C14 O3 C13 O4 176.55(16) . . . . ?
C14 O3 C13 C12 -2.55(18) . . . . ?
C15 C12 C13 O4 -176.80(18) . . . . ?
C11 C12 C13 O4 3.1(3) . . . . ?
C15 C12 C13 O3 2.19(18) . . . . ?
C11 C12 C13 O3 -177.92(16) . . . . ?
C13 O3 C14 C15 1.94(18) . . . . ?
C11 C12 C15 C16 -0.8(2) . . . . ?
C13 C12 C15 C16 179.07(15) . . . . ?
C11 C12 C15 C14 179.14(15) . . . . ?
C13 C12 C15 C14 -0.96(18) . . . . ?
O3 C14 C15 C12 -0.52(18) . . . . ?
O3 C14 C15 C16 179.45(17) . . . . ?
C12 C15 C16 C17 0.6(2) . . . . ?
C14 C15 C16 C17 -179.38(17) . . . . ?
C11 C10 C17 C16 -0.3(2) . . . . ?
C9 C10 C17 C16 176.45(15) . . . . ?
C15 C16 C17 C10 0.0(2) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30653925
