#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/42/2224231.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_2224231
loop_
_publ_author_name
'Ling, Chun-Sheng'
'Wang, Xu'
'Liu, Yun'
'Wu, Qiang'
_publ_section_title
;3,3'-(1,3,5,7-Tetraoxo-2,3,6,7-tetrahydro-1H,5H-pyrrolo[3,4-f]isoindole-2,6-diyl)dipropanoic
 acid N,N-dimethylformamide disolvate
;
_journal_coeditor_code           HB5179
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2975
_journal_paper_doi               10.1107/S1600536809045437
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C16 H12 N2 O8, 2C3 H7 N O'
_chemical_formula_moiety         'C16 H12 N2 O8, 2(C3 H7 N O)'
_chemical_formula_sum            'C22 H26 N4 O10'
_chemical_formula_weight         506.47
_chemical_name_systematic
;
3,3'-(1,3,5,7-Tetraoxo-2,3,6,7-tetrahydro-1H,5H-
pyrrolo[3,4-f]isoindole-2,6-diyl)dipropanoic acid
N,N-dimethylformamide solvate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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                 118.774(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   12.542(8)
_cell_length_b                   8.611(6)
_cell_length_c                   12.902(9)
_cell_measurement_reflns_used    2660
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      23.67
_cell_measurement_theta_min      2.97
_cell_volume                     1221.4(14)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2001)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker SMART CCD'
_diffrn_measurement_method       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  0.0371
_diffrn_reflns_av_sigmaI/netI    0.0263
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            12363
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.85
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       slab
_exptl_crystal_F_000             532
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.442
_refine_diff_density_min         -0.295
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         2386
_refine_ls_number_restraints     15
_refine_ls_restrained_S_all      1.215
_refine_ls_R_factor_all          0.0663
_refine_ls_R_factor_gt           0.0468
_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)+(0.0551P)²+0.5597P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1184
_refine_ls_wR_factor_ref         0.1329
_reflns_number_gt                1745
_reflns_number_total             2386
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb5179.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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 'Monoclinic' changed to 'monoclinic'
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 
;
_cod_original_cell_volume        1221.3(14)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2224231
_cod_database_fobs_code          2224231
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, 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
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.2286(2) 0.3041(3) -0.14930(17) 0.0847(7) Uani d U 1 . .
O O2 0.3228(2) 0.5093(3) -0.16182(17) 0.0896(8) Uani d U 1 . .
H H2 0.2861 0.4876 -0.2324 0.134 Uiso d R 1 . .
O O3 0.22033(16) 0.5402(2) 0.20189(14) 0.0502(5) Uani d . 1 . .
O O4 0.55406(18) 0.2430(2) 0.29251(15) 0.0579(5) Uani d . 1 . .
O O5 0.2066(2) 1.0088(2) 1.11020(15) 0.0651(6) Uani d . 1 . .
C C1 0.2949(2) 0.4100(3) -0.1032(2) 0.0487(6) Uani d U 1 . .
C C2 0.3578(3) 0.4407(4) 0.0263(2) 0.0575(7) Uani d . 1 . .
H H2B 0.3407 0.5465 0.0395 0.069 Uiso calc R 1 . .
H H2C 0.4449 0.4321 0.0564 0.069 Uiso calc R 1 . .
C C3 0.3212(3) 0.3327(3) 0.09466(19) 0.0479(6) Uani d . 1 . .
H H3A 0.2332 0.3320 0.0597 0.057 Uiso calc R 1 . .
H H3B 0.3475 0.2281 0.0903 0.057 Uiso calc R 1 . .
C C4 0.3193(2) 0.4830(3) 0.26018(19) 0.0388(5) Uani d . 1 . .
C C5 0.4876(2) 0.3319(3) 0.30588(19) 0.0403(5) Uani d . 1 . .
C C6 0.5071(2) 0.4122(3) 0.41634(19) 0.0366(5) Uani d . 1 . .
C C7 0.6041(2) 0.4039(3) 0.5291(2) 0.0396(5) Uani d . 1 . .
H H7A 0.6714 0.3412 0.5482 0.048 Uiso calc R 1 . .
C C8 0.5939(2) 0.4955(3) 0.61186(18) 0.0368(5) Uani d . 1 . .
C C9 0.1607(3) 0.8835(4) 1.0674(2) 0.0522(7) Uani d . 1 . .
H H9A 0.170(3) 0.794(4) 1.119(3) 0.066(8) Uiso d . 1 . .
C C10 0.0679(3) 0.9775(4) 0.8676(3) 0.0717(9) Uani d . 1 . .
H H10A 0.1090 1.0710 0.9071 0.108 Uiso calc R 1 . .
H H10B -0.0182 0.9958 0.8254 0.108 Uiso calc R 1 . .
H H10C 0.0955 0.9462 0.8131 0.108 Uiso calc R 1 . .
C C11 0.0398(4) 0.7052(5) 0.9101(4) 0.1117(16) Uani d . 1 . .
H H11A 0.0643 0.6347 0.9753 0.168 Uiso calc R 1 . .
H H11B 0.0663 0.6662 0.8566 0.168 Uiso calc R 1 . .
H H11C -0.0472 0.7148 0.8695 0.168 Uiso calc R 1 . .
N N1 0.37472(18) 0.3802(2) 0.21817(16) 0.0416(5) Uani d . 1 . .
N N2 0.0942(2) 0.8560(3) 0.95392(19) 0.0558(6) Uani 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 0.0016 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 O2 H2 . . 109.5 ?
O1 C1 O2 . . 122.5(2) ?
O1 C1 C2 . . 124.4(2) ?
O2 C1 C2 . . 113.1(2) ?
C1 C2 C3 . . 113.8(2) ?
C1 C2 H2B . . 108.8 ?
C3 C2 H2B . . 108.8 ?
C1 C2 H2C . . 108.8 ?
C3 C2 H2C . . 108.8 ?
H2B C2 H2C . . 107.7 ?
N1 C3 C2 . . 111.0(2) ?
N1 C3 H3A . . 109.4 ?
C2 C3 H3A . . 109.4 ?
N1 C3 H3B . . 109.4 ?
C2 C3 H3B . . 109.4 ?
H3A C3 H3B . . 108.0 ?
O3 C4 N1 . . 125.2(2) ?
O3 C4 C8 . 3_666 128.8(2) ?
N1 C4 C8 . 3_666 106.0(2) ?
O4 C5 N1 . . 125.5(2) ?
O4 C5 C6 . . 128.6(2) ?
N1 C5 C6 . . 105.9(2) ?
C7 C6 C8 . 3_666 122.5(2) ?
C7 C6 C5 . . 129.7(2) ?
C8 C6 C5 3_666 . 107.8(2) ?
C6 C7 C8 . . 115.0(2) ?
C6 C7 H7A . . 122.5 ?
C8 C7 H7A . . 122.5 ?
C7 C8 C6 . 3_666 122.4(2) ?
C7 C8 C4 . 3_666 129.6(2) ?
C6 C8 C4 3_666 3_666 107.94(19) ?
O5 C9 N2 . . 124.9(3) ?
O5 C9 H9A . . 120.7(17) ?
N2 C9 H9A . . 114.4(18) ?
N2 C10 H10A . . 109.5 ?
N2 C10 H10B . . 109.5 ?
H10A C10 H10B . . 109.5 ?
N2 C10 H10C . . 109.5 ?
H10A C10 H10C . . 109.5 ?
H10B C10 H10C . . 109.5 ?
N2 C11 H11A . . 109.5 ?
N2 C11 H11B . . 109.5 ?
H11A C11 H11B . . 109.5 ?
N2 C11 H11C . . 109.5 ?
H11A C11 H11C . . 109.5 ?
H11B C11 H11C . . 109.5 ?
C5 N1 C4 . . 112.35(19) ?
C5 N1 C3 . . 124.1(2) ?
C4 N1 C3 . . 123.5(2) ?
C9 N2 C10 . . 121.1(3) ?
C9 N2 C11 . . 121.6(3) ?
C10 N2 C11 . . 117.3(3) ?
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 . 1.184(3) ?
O2 C1 . 1.296(3) ?
O2 H2 . 0.8200 ?
O3 C4 . 1.204(3) ?
O4 C5 . 1.203(3) ?
O5 C9 . 1.222(3) ?
C1 C2 . 1.488(3) ?
C2 C3 . 1.498(4) ?
C2 H2B . 0.9700 ?
C2 H2C . 0.9700 ?
C3 N1 . 1.458(3) ?
C3 H3A . 0.9700 ?
C3 H3B . 0.9700 ?
C4 N1 . 1.387(3) ?
C4 C8 3_666 1.488(3) ?
C5 N1 . 1.384(3) ?
C5 C6 . 1.495(3) ?
C6 C7 . 1.378(3) ?
C6 C8 3_666 1.387(3) ?
C7 C8 . 1.382(3) ?
C7 H7A . 0.9300 ?
C8 C6 3_666 1.387(3) ?
C8 C4 3_666 1.488(3) ?
C9 N2 . 1.311(3) ?
C9 H9A . 0.99(3) ?
C10 N2 . 1.445(4) ?
C10 H10A . 0.9600 ?
C10 H10B . 0.9600 ?
C10 H10C . 0.9600 ?
C11 N2 . 1.449(4) ?
C11 H11A . 0.9600 ?
C11 H11B . 0.9600 ?
C11 H11C . 0.9600 ?
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
O2 H2 O5 4_574 0.82 1.78 2.583(3) 166
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O1 C1 C2 C3 . . . . -5.3(4) ?
O2 C1 C2 C3 . . . . 176.6(3) ?
C1 C2 C3 N1 . . . . -173.2(2) ?
O4 C5 C6 C7 . . . . -0.5(4) ?
N1 C5 C6 C7 . . . . 179.4(2) ?
O4 C5 C6 C8 . . . 3_666 179.4(2) ?
N1 C5 C6 C8 . . . 3_666 -0.7(2) ?
C8 C6 C7 C8 3_666 . . . -0.7(4) ?
C5 C6 C7 C8 . . . . 179.2(2) ?
C6 C7 C8 C6 . . . 3_666 0.7(4) ?
C6 C7 C8 C4 . . . 3_666 -179.0(2) ?
O4 C5 N1 C4 . . . . 180.0(2) ?
C6 C5 N1 C4 . . . . 0.0(3) ?
O4 C5 N1 C3 . . . . -1.9(4) ?
C6 C5 N1 C3 . . . . 178.2(2) ?
O3 C4 N1 C5 . . . . -179.1(2) ?
C8 C4 N1 C5 3_666 . . . 0.6(2) ?
O3 C4 N1 C3 . . . . 2.7(4) ?
C8 C4 N1 C3 3_666 . . . -177.6(2) ?
C2 C3 N1 C5 . . . . -88.7(3) ?
C2 C3 N1 C4 . . . . 89.2(3) ?
O5 C9 N2 C10 . . . . -0.8(5) ?
O5 C9 N2 C11 . . . . -178.1(4) ?
