#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/07/2210742.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_2210742
loop_
_publ_author_name
'Mizuguchi, Jin'
'Arai, Ayako'
_publ_section_title
;
 3,3'-(1,4-Dioxopyrrolo[3,4-c]pyrrole-3,6-diyl)dibenzonitrile
 dimethylacetamide disolvate
;
_journal_coeditor_code           OB2060
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o4382
_journal_page_last               o4384
_journal_paper_doi               10.1107/S1600536806035677
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C20 H10 N4 O2 , 2C4 H9 N O'
_chemical_formula_moiety         'C20 H10 N4 O2 , 2C4 H9 N O'
_chemical_formula_sum            'C28 H28 N6 O4'
_chemical_formula_weight         512.56
_chemical_name_systematic
;3,3'-(1,4-dioxopyrrolo[3,4-c]pyrrole-3,6-diyl)dibenzonitrile
 dimethylacetamide
disolvate
;
_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'
_cell_angle_alpha                90.0000
_cell_angle_beta                 105.18(2)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            2
_cell_length_a                   16.129(5)
_cell_length_b                   4.020(5)
_cell_length_c                   20.676(6)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    296
_cell_measurement_theta_max      13.2
_cell_measurement_theta_min      10.5
_cell_volume                     1293.8(17)
_computing_cell_refinement       'MSC/AFC Diffractometer Control Software'
_computing_data_collection
'MSC/AFC Diffractometer Control Software (Rigaku/MSC, 2000)'
_computing_data_reduction        'CrystalStructure (Rigaku/MSC, 2005)'
_computing_molecular_graphics    'ORTEPIII (Burnett & Johnson, 1996)'
_computing_publication_material  CrystalStructure
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR2002 (Burla et al.,  2003)'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Rigaku AFC-7R'
_diffrn_measurement_method       ω/2θ
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.082
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            3078
_diffrn_reflns_theta_full        27.52
_diffrn_reflns_theta_max         27.52
_diffrn_standards_decay_%        22.0
_diffrn_standards_interval_count 0
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.997
_exptl_absorpt_correction_T_min  0.968
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al.,  1968)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             540.00
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.85
_refine_diff_density_min         -0.37
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.136
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     143
_refine_ls_number_reflns         2975
_refine_ls_R_factor_gt           0.1094
_refine_ls_shift/su_max          0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.1P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.3471
_reflns_number_gt                665
_reflns_number_total             2975
_reflns_threshold_expression     F²>2σ(F²)
_cod_data_source_file            ob2060.cif
_cod_data_source_block           I
_cod_database_code               2210742
_cod_database_fobs_code          2210742
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +x,+y,+z
2 -x,1/2+y,1/2-z
3 -x,-y,-z
4 +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
O O1 0.5981(3) 0.3044(16) 0.6276(2) 0.0608(18) Uani d . 1.00
O O2 0.7780(3) 0.6305(17) 0.5472(3) 0.0781(19) Uani d . 1.00
N N1 0.6219(3) 0.2455(16) 0.5222(2) 0.0434(18) Uani d . 1.00
N N2 0.8766(4) 0.525(2) 0.3587(4) 0.091(3) Uani d . 1.00
N N3 0.8872(6) 0.884(2) 0.6079(4) 0.117(3) Uani d . 1.00
C C1 0.6180(4) 0.127(2) 0.4033(3) 0.039(2) Uani d . 1.00
C C2 0.6974(4) 0.259(2) 0.4072(3) 0.046(2) Uani d . 1.00
C C3 0.7264(4) 0.274(2) 0.3508(3) 0.044(2) Uani d . 1.00
C C4 0.6792(5) 0.159(2) 0.2897(4) 0.058(2) Uani d . 1.00
C C5 0.6010(5) 0.020(2) 0.2856(3) 0.055(2) Uani d . 1.00
C C6 0.5666(4) 0.003(2) 0.3410(3) 0.045(2) Uani d . 1.00
C C7 0.5779(4) 0.109(2) 0.4604(3) 0.0365(19) Uani d . 1.00
C C8 0.5028(4) -0.0263(19) 0.4668(2) 0.0328(18) Uani d . 1.00
C C9 0.5737(4) 0.204(2) 0.5695(3) 0.041(2) Uani d . 1.00
C C10 0.8114(6) 0.409(2) 0.3552(4) 0.064(2) Uani d . 1.00
C C11 0.8172(8) 0.764(3) 0.6047(6) 0.123(5) Uani d . 1.00
C C12 0.7842(5) 0.787(2) 0.6674(4) 0.081(2) Uani d . 1.00
C C13 0.9418(5) 1.030(2) 0.6689(4) 0.079(3) Uani d . 1.00
C C14 0.9180(5) 0.879(2) 0.5419(4) 0.090(3) Uani d . 1.00
H H1N 0.6712 0.3412 0.5302 0.052 Uiso c R 1.00
H H2 0.7313 0.3378 0.4478 0.055 Uiso c R 1.00
H H4 0.7002 0.1759 0.2520 0.070 Uiso c R 1.00
H H5 0.5695 -0.0669 0.2448 0.066 Uiso c R 1.00
H H6 0.5123 -0.0849 0.3373 0.054 Uiso c R 1.00
H H12A 0.8082 0.9790 0.6902 0.097 Uiso c . 1.00
H H12B 0.7250 0.7920 0.6536 0.097 Uiso c . 1.00
H H12C 0.8048 0.5937 0.6930 0.097 Uiso c . 1.00
H H13A 0.9301 1.2642 0.6698 0.098 Uiso c R 1.00
H H13B 1.0011 0.9980 0.6697 0.098 Uiso c R 1.00
H H13C 0.9302 0.9250 0.7073 0.098 Uiso c R 1.00
H H14A 0.9482 0.6755 0.5396 0.100 Uiso c R 1.00
H H14B 0.9555 1.0644 0.5419 0.100 Uiso c R 1.00
H H14C 0.8690 0.8944 0.5038 0.100 Uiso c R 1.00
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.003 0.002
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.000 0.000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
N N 0.006 0.003
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.011 0.006
;
International Tables for Crystallography
(1992, 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
C7 N1 C9 . . 110.3(5) yes
C7 N1 H1N . . 124.9 ?
C9 N1 H1N . . 124.9 ?
C11 N3 C13 . . 123.3(11) ?
C11 N3 C14 . . 116.7(9) ?
C13 N3 C14 . . 120.0(8) ?
C2 C1 C6 . . 120.1(7) ?
C2 C1 C7 . . 124.4(6) ?
C6 C1 C7 . . 115.5(6) ?
C1 C2 C3 . . 119.4(6) ?
C1 C2 H2 . . 120.3 ?
C3 C2 H2 . . 120.3 ?
C2 C3 C4 . . 122.7(7) ?
C2 C3 C10 . . 119.3(6) ?
C4 C3 C10 . . 118.0(7) ?
C3 C4 C5 . . 118.5(8) ?
C3 C4 H4 . . 120.8 ?
C5 C4 H4 . . 120.8 ?
C4 C5 C6 . . 121.8(7) ?
C4 C5 H5 . . 119.1 ?
C6 C5 H5 . . 119.1 ?
C1 C6 C5 . . 117.6(6) ?
C1 C6 H6 . . 121.2 ?
C5 C6 H6 . . 121.2 ?
N1 C7 C1 . . 118.9(5) ?
N1 C7 C8 . . 108.6(6) yes
C1 C7 C8 . . 132.5(6) ?
C7 C8 C8 . 3_656 108.5(5) yes
C7 C8 C9 . 3_656 143.3(6) yes
C8 C8 C9 3_656 3_656 108.2(6) ?
O1 C9 N1 . . 123.0(6) yes
O1 C9 C8 . 3_656 132.6(7) ?
N1 C9 C8 . 3_656 104.4(5) yes
N2 C10 C3 . . 177.6(11) ?
O2 C11 N3 . . 115.8(12) ?
O2 C11 C12 . . 127.0(11) ?
N3 C11 C12 . . 117.1(10) ?
C11 C12 H12A . . 106.7 ?
C11 C12 H12B . . 107.6 ?
C11 C12 H12C . . 106.0 ?
H12A C12 H12B . . 113.3 ?
H12A C12 H12C . . 110.9 ?
H12B C12 H12C . . 111.9 ?
N3 C13 H13A . . 109.5 ?
N3 C13 H13B . . 109.5 ?
N3 C13 H13C . . 109.5 ?
H13A C13 H13B . . 109.5 ?
H13A C13 H13C . . 109.5 ?
H13B C13 H13C . . 109.5 ?
N3 C14 H14A . . 109.5 ?
N3 C14 H14B . . 109.5 ?
N3 C14 H14C . . 109.5 ?
H14A C14 H14B . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 109.5 ?
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 C9 . 1.230(8) yes
O2 C11 . 1.307(14) ?
N1 C7 . 1.400(8) yes
N1 C9 . 1.410(10) yes
N1 H1N . 0.860 ?
N2 C10 . 1.136(13) ?
N3 C11 . 1.213(17) ?
N3 C13 . 1.460(12) ?
N3 C14 . 1.568(15) ?
C1 C2 . 1.370(10) ?
C1 C6 . 1.426(9) ?
C1 C7 . 1.490(10) ?
C2 C3 . 1.365(12) ?
C2 H2 . 0.930 ?
C3 C4 . 1.373(10) ?
C3 C10 . 1.456(13) ?
C4 C5 . 1.363(12) ?
C4 H4 . 0.930 ?
C5 C6 . 1.398(12) ?
C5 H5 . 0.930 ?
C6 H6 . 0.930 ?
C7 C8 . 1.365(10) yes
C8 C8 3_656 1.417(9) yes
C8 C9 3_656 1.452(9) yes
C11 C12 . 1.528(18) ?
C13 H13A . 0.960 ?
C13 H13B . 0.960 ?
C13 H13C . 0.960 ?
C14 H14A . 0.960 ?
C14 H14B . 0.960 ?
C14 H14C . 0.960 ?
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_2
O1 H4 2.667 4_555
O1 H5 2.790 4_555
O1 H12B 2.783 .
O2 H1N 2.030 .
O2 H2 2.316 .
O2 H12B 2.642 .
N3 H12A 2.409 .
N3 H12C 2.730 .
C11 H12A 2.007 .
C11 H12B 2.010 .
C11 H12C 2.009 .
C12 H12A 0.934 .
C12 H12B 0.923 .
C12 H12C 0.950 .
C13 H12A 2.319 .
H1N O2 2.030 .
H2 O2 2.316 .
H4 O1 2.667 4_554
H4 H12A 2.785 4_564
H4 H12C 2.567 4_554
H5 O1 2.790 4_554
H5 H6 2.790 2_645
H5 H6 2.684 2_655
H6 H5 2.684 2_645
H6 H5 2.790 2_655
H12A N3 2.409 .
H12A C11 2.007 .
H12A C12 0.934 .
H12A C13 2.319 .
H12A H4 2.785 4_565
H12A H12B 1.5514 .
H12A H12C 1.5514 .
H12A H12C 2.4727 1_565
H12A H13A 2.406 .
H12A H13C 1.919 .
H12B O1 2.783 .
H12B O2 2.642 .
H12B C11 2.010 .
H12B C12 0.923 .
H12B H12A 1.5514 .
H12B H12C 1.5514 .
H12C N3 2.730 .
H12C C11 2.009 .
H12C C12 0.950 .
H12C H4 2.567 4_555
H12C H12A 2.4727 1_545
H12C H12A 1.5514 .
H12C H12B 1.5514 .
H12C H13A 2.563 1_545
H12C H13C 2.375 .
H13A H12A 2.406 .
H13A H12C 2.563 1_565
H13A H13C 2.767 1_565
H13C H12A 1.919 .
H13C H12C 2.375 .
H13C H13A 2.767 1_545
H14A H14B 2.459 1_545
H14A H14B 2.779 3_776
H14B H14A 2.459 1_565
H14B H14A 2.779 3_776
H14B H14B 2.575 3_776
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H1N O2 0.860 2.030 2.884(8) 171.6 yes
