#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/8/10/22/8102203.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_8102203
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)-3-(2-oxopropyl)isoindolin-1-one,
 C19H15NO4
;
_journal_issue                   1
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              27
_journal_volume                  223
_journal_year                    2008
_chemical_formula_moiety         'C19 H15 N O4'
_chemical_formula_sum            'C19 H15 N O4'
_chemical_formula_weight         321.32
_chemical_name_systematic
; 
2-(3-oxo-1,3-dihydro-2-benzofuran-5-yl)-3-(2-oxopropyl)isoindolin-1-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                90.414(4)
_cell_angle_beta                 94.375(7)
_cell_angle_gamma                98.476(5)
_cell_formula_units_Z            2
_cell_length_a                   6.6649(13)
_cell_length_b                   8.2483(14)
_cell_length_c                   13.659(3)
_cell_measurement_reflns_used    1822
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      30.1
_cell_measurement_theta_min      2.5
_cell_volume                     740.4(3)
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.028
_diffrn_reflns_av_sigmaI/netI    0.021
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            14706
_diffrn_reflns_theta_full        26.5
_diffrn_reflns_theta_max         26.50
_diffrn_reflns_theta_min         2.50
_diffrn_standards_decay_%        '< 1'
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.917
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Higashi, 1995)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.441
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.57
_refine_diff_density_min         -0.47
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.09
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3071
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.09
_refine_ls_R_factor_all          0.057
_refine_ls_R_factor_gt           0.054
_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)+(0.0644P)²+0.3451P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.133
_refine_ls_wR_factor_ref         0.136
_reflns_number_gt                2903
_reflns_number_total             3071
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            1267-2130.cff
_cod_data_source_block           shelxl
_cod_original_cell_volume        740.4(2)
_cod_original_sg_symbol_Hall     '-P 1 '
_cod_original_sg_symbol_H-M      ' P -1'
_cod_database_code               8102203
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 -0.29996(18) 0.47723(16) 0.68269(9) 0.0365(3) Uani 1 2 i d . . .
O2 O 0.5787(3) 0.8781(2) 0.64466(15) 0.0752(6) Uani 1 2 i d . . .
O3 O 0.02839(19) 0.16510(15) 1.07219(9) 0.0340(3) Uani 1 2 i d . . .
O4 O -0.28357(19) 0.20139(16) 1.01244(9) 0.0362(3) Uani 1 2 i d . . .
N1 N 0.0470(2) 0.57063(16) 0.71011(10) 0.0263(3) Uani 1 2 i d . . .
C1 C -0.1421(2) 0.5559(2) 0.65794(12) 0.0278(4) Uani 1 2 i d . . .
C2 C -0.1117(3) 0.6509(2) 0.56793(12) 0.0283(4) Uani 1 2 i d . . .
C3 C -0.2518(3) 0.6693(2) 0.48954(13) 0.0322(4) Uani 1 2 i d . . .
H3 H -0.3903 0.6210 0.4898 0.039 Uiso 1 2 i calc R . .
C4 C -0.1819(3) 0.7606(2) 0.41126(13) 0.0364(4) Uani 1 2 i d . . .
H4 H -0.2733 0.7737 0.3560 0.044 Uiso 1 2 i calc R . .
C5 C 0.0203(3) 0.8336(2) 0.41219(13) 0.0367(4) Uani 1 2 i d . . .
H5 H 0.0642 0.8965 0.3577 0.044 Uiso 1 2 i calc R . .
C6 C 0.1593(3) 0.8164(2) 0.49100(12) 0.0328(4) Uani 1 2 i d . . .
H6 H 0.2971 0.8668 0.4915 0.039 Uiso 1 2 i calc R . .
C7 C 0.0898(3) 0.7232(2) 0.56900(12) 0.0272(4) Uani 1 2 i d . . .
C8 C 0.2033(2) 0.6828(2) 0.66263(12) 0.0268(4) Uani 1 2 i d . . .
H8 H 0.3189 0.6243 0.6478 0.032 Uiso 1 2 i calc R . .
C9 C 0.2808(3) 0.8324(2) 0.72998(12) 0.0299(4) Uani 1 2 i d . . .
H9A H 0.1813 0.9105 0.7231 0.036 Uiso 1 2 i calc R . .
H9B H 0.2862 0.7959 0.7989 0.036 Uiso 1 2 i calc R . .
C10 C 0.4859(3) 0.9209(2) 0.71016(14) 0.0370(4) Uani 1 2 i d . . .
C11 C 0.5704(3) 1.0679(2) 0.77368(15) 0.0429(5) Uani 1 2 i d . . .
H11A H 0.7075 1.0562 0.8013 0.064 Uiso 1 2 i calc R . .
H11B H 0.4822 1.0767 0.8271 0.064 Uiso 1 2 i calc R . .
H11C H 0.5767 1.1669 0.7341 0.064 Uiso 1 2 i calc R . .
C12 C 0.0986(2) 0.48350(19) 0.79431(11) 0.0255(3) Uani 1 2 i d . . .
C13 C 0.3050(2) 0.4727(2) 0.81952(13) 0.0298(4) Uani 1 2 i d . . .
H13 H 0.4046 0.5241 0.7791 0.036 Uiso 1 2 i calc R . .
C14 C 0.3672(3) 0.3898(2) 0.90116(13) 0.0310(4) Uani 1 2 i d . . .
H14 H 0.5074 0.3851 0.9174 0.037 Uiso 1 2 i calc R . .
C15 C 0.2204(3) 0.3136(2) 0.95874(12) 0.0282(4) Uani 1 2 i d . . .
C16 C 0.2375(3) 0.2138(2) 1.04905(13) 0.0342(4) Uani 1 2 i d . . .
H16A H 0.3035 0.1166 1.0363 0.041 Uiso 1 2 i calc R . .
H16B H 0.3171 0.2798 1.1035 0.041 Uiso 1 2 i calc R . .
C17 C -0.1023(3) 0.2280(2) 1.00609(12) 0.0285(4) Uani 1 2 i d . . .
C18 C 0.0183(2) 0.32208(19) 0.93370(12) 0.0260(3) Uani 1 2 i d . . .
C19 C -0.0485(2) 0.40651(19) 0.85278(12) 0.0258(3) Uani 1 2 i d . . .
H19 H -0.1890 0.4116 0.8379 0.031 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
C17 O3 C16 110.56(13) . . ?
C1 N1 C12 126.65(14) . . ?
C1 N1 C8 112.13(13) . . ?
C12 N1 C8 121.05(13) . . ?
O1 C1 N1 125.90(15) . . ?
O1 C1 C2 127.88(16) . . ?
N1 C1 C2 106.21(14) . . ?
C7 C2 C3 121.69(16) . . ?
C7 C2 C1 109.43(15) . . ?
C3 C2 C1 128.86(16) . . ?
C4 C3 C2 117.43(17) . . ?
C4 C3 H3 121.3 . . ?
C2 C3 H3 121.3 . . ?
C3 C4 C5 120.99(17) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 H4 119.5 . . ?
C4 C5 C6 121.41(17) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C7 C6 C5 117.62(17) . . ?
C7 C6 H6 121.2 . . ?
C5 C6 H6 121.2 . . ?
C2 C7 C6 120.84(16) . . ?
C2 C7 C8 109.63(14) . . ?
C6 C7 C8 129.53(16) . . ?
N1 C8 C7 102.37(13) . . ?
N1 C8 C9 109.95(13) . . ?
C7 C8 C9 113.86(14) . . ?
N1 C8 H8 110.1 . . ?
C7 C8 H8 110.1 . . ?
C9 C8 H8 110.1 . . ?
C10 C9 C8 114.84(14) . . ?
C10 C9 H9A 108.6 . . ?
C8 C9 H9A 108.6 . . ?
C10 C9 H9B 108.6 . . ?
C8 C9 H9B 108.6 . . ?
H9A C9 H9B 107.5 . . ?
O2 C10 C9 121.59(17) . . ?
O2 C10 C11 120.97(18) . . ?
C9 C10 C11 117.43(16) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C19 C12 N1 121.99(15) . . ?
C19 C12 C13 119.17(15) . . ?
N1 C12 C13 118.83(14) . . ?
C14 C13 C12 122.11(15) . . ?
C14 C13 H13 118.9 . . ?
C12 C13 H13 118.9 . . ?
C15 C14 C13 118.37(16) . . ?
C15 C14 H14 120.8 . . ?
C13 C14 H14 120.8 . . ?
C18 C15 C14 119.73(16) . . ?
C18 C15 C16 109.00(15) . . ?
C14 C15 C16 131.27(16) . . ?
O3 C16 C15 104.25(13) . . ?
O3 C16 H16A 110.9 . . ?
C15 C16 H16A 110.9 . . ?
O3 C16 H16B 110.9 . . ?
C15 C16 H16B 110.9 . . ?
H16A C16 H16B 108.9 . . ?
O4 C17 O3 120.90(15) . . ?
O4 C17 C18 130.78(16) . . ?
O3 C17 C18 108.31(14) . . ?
C15 C18 C19 123.15(15) . . ?
C15 C18 C17 107.87(14) . . ?
C19 C18 C17 128.98(15) . . ?
C18 C19 C12 117.46(15) . . ?
C18 C19 H19 121.3 . . ?
C12 C19 H19 121.3 . . ?
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 1.224(2) . ?
O2 C10 1.205(2) . ?
O3 C17 1.365(2) . ?
O3 C16 1.451(2) . ?
O4 C17 1.206(2) . ?
N1 C1 1.388(2) . ?
N1 C12 1.408(2) . ?
N1 C8 1.480(2) . ?
C1 C2 1.474(2) . ?
C2 C7 1.385(2) . ?
C2 C3 1.391(2) . ?
C3 C4 1.383(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.392(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.387(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.387(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.500(2) . ?
C8 C9 1.536(2) . ?
C8 H8 1.0000 . ?
C9 C10 1.496(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.500(3) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C19 1.395(2) . ?
C12 C13 1.408(2) . ?
C13 C14 1.381(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.383(2) . ?
C14 H14 0.9500 . ?
C15 C18 1.376(2) . ?
C15 C16 1.494(2) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.474(2) . ?
C18 C19 1.390(2) . ?
C19 H19 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
C12 N1 C1 O1 8.2(3) . . . . ?
C8 N1 C1 O1 -176.54(16) . . . . ?
C12 N1 C1 C2 -170.96(14) . . . . ?
C8 N1 C1 C2 4.33(18) . . . . ?
O1 C1 C2 C7 179.26(17) . . . . ?
N1 C1 C2 C7 -1.63(18) . . . . ?
O1 C1 C2 C3 -2.1(3) . . . . ?
N1 C1 C2 C3 177.01(17) . . . . ?
C7 C2 C3 C4 1.1(3) . . . . ?
C1 C2 C3 C4 -177.37(16) . . . . ?
C2 C3 C4 C5 -1.2(3) . . . . ?
C3 C4 C5 C6 0.6(3) . . . . ?
C4 C5 C6 C7 0.3(3) . . . . ?
C3 C2 C7 C6 -0.3(2) . . . . ?
C1 C2 C7 C6 178.41(15) . . . . ?
C3 C2 C7 C8 179.65(15) . . . . ?
C1 C2 C7 C8 -1.60(18) . . . . ?
C5 C6 C7 C2 -0.4(2) . . . . ?
C5 C6 C7 C8 179.66(17) . . . . ?
C1 N1 C8 C7 -5.11(17) . . . . ?
C12 N1 C8 C7 170.47(13) . . . . ?
C1 N1 C8 C9 116.22(15) . . . . ?
C12 N1 C8 C9 -68.19(18) . . . . ?
C2 C7 C8 N1 3.94(17) . . . . ?
C6 C7 C8 N1 -176.08(16) . . . . ?
C2 C7 C8 C9 -114.67(15) . . . . ?
C6 C7 C8 C9 65.3(2) . . . . ?
N1 C8 C9 C10 158.15(14) . . . . ?
C7 C8 C9 C10 -87.66(18) . . . . ?
C8 C9 C10 O2 1.5(3) . . . . ?
C8 C9 C10 C11 -179.85(16) . . . . ?
C1 N1 C12 C19 -19.6(2) . . . . ?
C8 N1 C12 C19 165.50(14) . . . . ?
C1 N1 C12 C13 159.79(16) . . . . ?
C8 N1 C12 C13 -15.1(2) . . . . ?
C19 C12 C13 C14 -0.8(3) . . . . ?
N1 C12 C13 C14 179.81(15) . . . . ?
C12 C13 C14 C15 0.8(3) . . . . ?
C13 C14 C15 C18 0.0(2) . . . . ?
C13 C14 C15 C16 178.85(17) . . . . ?
C17 O3 C16 C15 -0.79(18) . . . . ?
C18 C15 C16 O3 0.64(19) . . . . ?
C14 C15 C16 O3 -178.28(17) . . . . ?
C16 O3 C17 O4 179.90(16) . . . . ?
C16 O3 C17 C18 0.65(18) . . . . ?
C14 C15 C18 C19 -0.9(3) . . . . ?
C16 C15 C18 C19 180.00(15) . . . . ?
C14 C15 C18 C17 178.79(14) . . . . ?
C16 C15 C18 C17 -0.28(19) . . . . ?
O4 C17 C18 C15 -179.37(18) . . . . ?
O3 C17 C18 C15 -0.22(18) . . . . ?
O4 C17 C18 C19 0.3(3) . . . . ?
O3 C17 C18 C19 179.47(15) . . . . ?
C15 C18 C19 C12 1.0(2) . . . . ?
C17 C18 C19 C12 -178.70(15) . . . . ?
N1 C12 C19 C18 179.29(14) . . . . ?
C13 C12 C19 C18 -0.1(2) . . . . ?
