#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/26/2202678.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_2202678
loop_
_publ_author_name
'Shi, Da-Xin'
'Feng, Ya-Qing'
'Li, Xiao-Fang'
'Zhou, Li-shan'
_publ_section_title
2-Benzyl-5-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)-2,3-dihydro-1H-isoindole-1,3-dione
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1068
_journal_page_last               o1069
_journal_paper_doi               10.1107/S1600536803014181
_journal_volume                  59
_journal_year                    2003
_chemical_formula_iupac          'C19 H12 N2 O4'
_chemical_formula_moiety         'C19 H12 N2 O4'
_chemical_formula_sum            'C19 H12 N2 O4'
_chemical_formula_weight         332.31
_chemical_name_systematic
;
2-Benzyl-5-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)-2,3-dihydro-
1H-isoindole-1,3-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'
_cell_angle_alpha                112.607(6)
_cell_angle_beta                 94.050(6)
_cell_angle_gamma                95.755(6)
_cell_formula_units_Z            2
_cell_length_a                   5.061(2)
_cell_length_b                   11.803(4)
_cell_length_c                   14.186(5)
_cell_measurement_reflns_used    997
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.32
_cell_measurement_theta_min      3.13
_cell_volume                     772.8(5)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        'SAINT (Bruker, 1998)'
_computing_molecular_graphics    'SHELXTL (Bruker, 1998)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker SMART CCD'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0139
_diffrn_reflns_av_sigmaI/netI    0.0309
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            3218
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         1.57
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  0.985
_exptl_absorpt_correction_T_min  0.976
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.428
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    none
_exptl_crystal_description       plate
_exptl_crystal_F_000             344
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.165
_refine_diff_density_min         -0.200
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         2700
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0549
_refine_ls_R_factor_gt           0.0377
_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)+(0.0604P)²+0.1101P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1149
_reflns_number_gt                2082
_reflns_number_total             2700
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh6074.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not mesaured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_database_code               2202678
_cod_database_fobs_code          2202678
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_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
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
O1 0.2581(3) 0.95332(12) 0.03582(12) 0.0541(4) Uani d . 1 . . O
O2 0.1897(4) 0.53200(13) -0.07670(12) 0.0703(5) Uani d . 1 . . O
O3 0.4487(3) 0.56491(13) 0.30525(11) 0.0582(4) Uani d . 1 . . O
O4 1.1962(3) 0.85166(14) 0.39137(12) 0.0584(4) Uani d . 1 . . O
N1 0.2824(3) 0.74661(13) 0.00293(12) 0.0403(4) Uani d . 1 . . N
N2 0.8442(3) 0.69878(14) 0.36710(12) 0.0420(4) Uani d . 1 . . N
C1 0.1916(4) 0.84475(18) -0.01689(15) 0.0420(5) Uani d . 1 . . C
C2 -0.0020(4) 0.7862(2) -0.11143(16) 0.0527(5) Uani d . 1 . . C
H2 -0.0946 0.8288 -0.1432 0.063 Uiso calc R 1 . . H
C3 -0.0225(5) 0.6654(2) -0.14331(16) 0.0569(6) Uani d . 1 . . C
H3 -0.1313 0.6088 -0.2012 0.068 Uiso calc R 1 . . H
C4 0.1553(4) 0.63295(18) -0.07246(15) 0.0484(5) Uani d . 1 . . C
C5 0.4677(4) 0.76075(16) 0.08860(13) 0.0361(4) Uani d . 1 . . C
C6 0.6924(4) 0.85051(17) 0.11607(14) 0.0402(4) Uani d . 1 . . C
H6 0.7183 0.8992 0.0784 0.048 Uiso calc R 1 . . H
C7 0.8772(4) 0.86784(17) 0.19883(15) 0.0417(5) Uani d . 1 . . C
H7 1.0280 0.9271 0.2171 0.050 Uiso calc R 1 . . H
C8 0.8309(3) 0.79450(16) 0.25334(13) 0.0365(4) Uani d . 1 . . C
C9 0.9886(4) 0.79070(17) 0.34436(15) 0.0417(4) Uani d . 1 . . C
C10 0.6109(4) 0.64521(16) 0.30038(14) 0.0410(5) Uani d . 1 . . C
C11 0.6050(4) 0.70617(15) 0.22588(13) 0.0362(4) Uani d . 1 . . C
C12 0.4192(4) 0.68696(16) 0.14388(14) 0.0390(4) Uani d . 1 . . C
H12 0.2685 0.6277 0.1261 0.047 Uiso calc R 1 . . H
C13 0.9164(4) 0.67065(18) 0.45678(15) 0.0467(5) Uani d . 1 . . C
H13A 1.1027 0.7031 0.4827 0.056 Uiso calc R 1 . . H
H13B 0.8965 0.5815 0.4360 0.056 Uiso calc R 1 . . H
C14 0.7450(4) 0.72543(16) 0.54179(14) 0.0398(4) Uani d . 1 . . C
C15 0.6449(4) 0.65706(18) 0.59523(15) 0.0493(5) Uani d . 1 . . C
H15 0.6836 0.5767 0.5787 0.059 Uiso calc R 1 . . H
C16 0.4883(5) 0.7074(2) 0.67279(17) 0.0575(6) Uani d . 1 . . C
H16 0.4224 0.6609 0.7082 0.069 Uiso calc R 1 . . H
C17 0.4292(5) 0.8259(2) 0.69785(17) 0.0571(6) Uani d . 1 . . C
H17 0.3224 0.8594 0.7497 0.069 Uiso calc R 1 . . H
C18 0.5291(5) 0.89469(19) 0.64582(17) 0.0555(6) Uani d . 1 . . C
H18 0.4912 0.9752 0.6631 0.067 Uiso calc R 1 . . H
C19 0.6849(4) 0.84494(18) 0.56838(16) 0.0491(5) Uani d . 1 . . C
H19 0.7506 0.8921 0.5334 0.059 Uiso calc R 1 . . H
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
C1 N1 C4 109.52(16) y
C1 N1 C5 124.88(15) ?
C4 N1 C5 125.56(15) ?
C10 N2 C9 112.12(15) y
C10 N2 C13 123.58(16) y
C9 N2 C13 124.05(17) ?
O1 C1 N1 125.19(19) ?
O1 C1 C2 128.94(18) ?
N1 C1 C2 105.85(16) ?
C3 C2 C1 109.50(19) ?
C3 C2 H2 125.2 ?
C1 C2 H2 125.2 ?
C2 C3 C4 109.33(19) y
C2 C3 H3 125.3 ?
C4 C3 H3 125.3 ?
O2 C4 N1 125.68(19) ?
O2 C4 C3 128.52(19) ?
N1 C4 C3 105.80(17) ?
C12 C5 C6 121.51(17) ?
C12 C5 N1 119.82(16) ?
C6 C5 N1 118.66(16) y
C7 C6 C5 120.71(17) ?
C7 C6 H6 119.6 ?
C5 C6 H6 119.6 ?
C8 C7 C6 117.98(17) ?
C8 C7 H7 121.0 ?
C6 C7 H7 121.0 ?
C7 C8 C11 120.81(17) ?
C7 C8 C9 130.76(17) ?
C11 C8 C9 108.42(16) ?
O4 C9 N2 125.07(18) ?
O4 C9 C8 129.39(18) ?
N2 C9 C8 105.54(16) ?
O3 C10 N2 124.77(17) ?
O3 C10 C11 128.95(19) ?
N2 C10 C11 106.27(15) ?
C12 C11 C8 122.29(16) ?
C12 C11 C10 130.08(17) ?
C8 C11 C10 107.62(16) ?
C11 C12 C5 116.69(17) ?
C11 C12 H12 121.7 ?
C5 C12 H12 121.7 ?
N2 C13 C14 112.12(15) y
N2 C13 H13A 109.2 ?
C14 C13 H13A 109.2 ?
N2 C13 H13B 109.2 ?
C14 C13 H13B 109.2 ?
H13A C13 H13B 107.9 ?
C19 C14 C15 118.46(18) ?
C19 C14 C13 120.88(17) ?
C15 C14 C13 120.66(16) ?
C16 C15 C14 120.48(18) ?
C16 C15 H15 119.8 ?
C14 C15 H15 119.8 ?
C17 C16 C15 120.34(19) ?
C17 C16 H16 119.8 ?
C15 C16 H16 119.8 ?
C16 C17 C18 119.6(2) ?
C16 C17 H17 120.2 ?
C18 C17 H17 120.2 ?
C19 C18 C17 120.32(19) ?
C19 C18 H18 119.8 ?
C17 C18 H18 119.8 ?
C18 C19 C14 120.81(19) ?
C18 C19 H19 119.6 ?
C14 C19 H19 119.6 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C1 . 1.207(2) y
O2 C4 . 1.201(2) y
O3 C10 . 1.216(2) y
O4 C9 . 1.203(2) y
N1 C1 . 1.404(2) ?
N1 C4 . 1.409(2) ?
N1 C5 . 1.427(2) y
N2 C10 . 1.386(3) ?
N2 C9 . 1.400(2) ?
N2 C13 . 1.465(2) y
C1 C2 . 1.484(3) ?
C2 C3 . 1.310(3) y
C2 H2 . 0.9300 ?
C3 C4 . 1.484(3) ?
C3 H3 . 0.9300 ?
C5 C12 . 1.394(2) ?
C5 C6 . 1.395(3) ?
C6 C7 . 1.385(3) ?
C6 H6 . 0.9300 ?
C7 C8 . 1.379(2) ?
C7 H7 . 0.9300 ?
C8 C11 . 1.390(3) ?
C8 C9 . 1.487(3) ?
C10 C11 . 1.490(2) ?
C11 C12 . 1.374(3) ?
C12 H12 . 0.9300 ?
C13 C14 . 1.512(3) ?
C13 H13A . 0.9700 ?
C13 H13B . 0.9700 ?
C14 C19 . 1.385(3) ?
C14 C15 . 1.387(3) ?
C15 C16 . 1.381(3) ?
C15 H15 . 0.9300 ?
C16 C17 . 1.374(3) ?
C16 H16 . 0.9300 ?
C17 C18 . 1.375(3) ?
C17 H17 . 0.9300 ?
C18 C19 . 1.376(3) ?
C18 H18 . 0.9300 ?
C19 H19 . 0.9300 ?
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
C4 N1 C1 O1 177.81(18) ?
C5 N1 C1 O1 -0.1(3) ?
C4 N1 C1 C2 -0.6(2) ?
C5 N1 C1 C2 -178.44(16) ?
O1 C1 C2 C3 -178.1(2) ?
N1 C1 C2 C3 0.2(2) ?
C1 C2 C3 C4 0.2(2) ?
C1 N1 C4 O2 -179.8(2) ?
C5 N1 C4 O2 -2.0(3) ?
C1 N1 C4 C3 0.7(2) ?
C5 N1 C4 C3 178.54(17) ?
C2 C3 C4 O2 180.0(2) ?
C2 C3 C4 N1 -0.5(2) ?
C1 N1 C5 C12 135.55(18) ?
C4 N1 C5 C12 -42.0(2) y
C1 N1 C5 C6 -43.3(2) y
C4 N1 C5 C6 139.11(19) ?
C12 C5 C6 C7 0.9(3) ?
N1 C5 C6 C7 179.81(15) ?
C5 C6 C7 C8 -0.5(3) ?
C6 C7 C8 C11 -0.1(3) ?
C6 C7 C8 C9 -179.96(17) ?
C10 N2 C9 O4 179.28(19) ?
C13 N2 C9 O4 4.9(3) ?
C10 N2 C9 C8 -0.53(19) ?
C13 N2 C9 C8 -174.90(15) ?
C7 C8 C9 O4 -0.3(3) ?
C11 C8 C9 O4 179.9(2) ?
C7 C8 C9 N2 179.50(17) ?
C11 C8 C9 N2 -0.35(19) ?
C9 N2 C10 O3 -178.54(18) ?
C13 N2 C10 O3 -4.1(3) ?
C9 N2 C10 C11 1.1(2) ?
C13 N2 C10 C11 175.54(15) ?
C7 C8 C11 C12 0.4(3) ?
C9 C8 C11 C12 -179.78(15) ?
C7 C8 C11 C10 -178.84(15) ?
C9 C8 C11 C10 1.02(19) ?
O3 C10 C11 C12 -0.8(3) ?
N2 C10 C11 C12 179.56(17) ?
O3 C10 C11 C8 178.33(19) ?
N2 C10 C11 C8 -1.33(19) ?
C8 C11 C12 C5 0.1(2) ?
C10 C11 C12 C5 179.06(16) ?
C6 C5 C12 C11 -0.7(2) ?
N1 C5 C12 C11 -179.56(15) ?
C10 N2 C13 C14 -71.9(2) ?
C9 N2 C13 C14 101.8(2) ?
N2 C13 C14 C19 -43.1(3) y
N2 C13 C14 C15 137.13(18) y
C19 C14 C15 C16 0.2(3) ?
C13 C14 C15 C16 -180.0(2) ?
C14 C15 C16 C17 0.1(3) ?
C15 C16 C17 C18 -0.6(3) ?
C16 C17 C18 C19 0.7(3) ?
C17 C18 C19 C14 -0.3(3) ?
C15 C14 C19 C18 -0.1(3) ?
C13 C14 C19 C18 -179.9(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21131646
