#------------------------------------------------------------------------------
#$Date: 2016-02-20 04:06:23 +0100 (Sat 20 de Feb de 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/78/2207845.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_2207845
loop_
_publ_author_name
'Hirota, Tsuyoshi'
'Imoda, Tomohiko'
'Takahashi, Hiroo'
'Mizuguchi, Jin'
_publ_section_title
;
 3,6-Di-3-pyridylpyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione
;
_journal_coeditor_code           OB6597
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o111
_journal_page_last               o113
_journal_paper_doi               10.1107/S160053680503984X
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C16 H10 N4 O2'
_chemical_formula_moiety         'C16 H10 N4 O2'
_chemical_formula_sum            'C16 H10 N4 O2'
_chemical_formula_weight         290.28
_chemical_name_systematic
;
3,6-Di-3-pyridylpyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione
;
_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                 98.823(9)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            2
_cell_length_a                   3.6616(5)
_cell_length_b                   15.0089(19)
_cell_length_c                   10.9791(13)
_cell_measurement_reflns_used    4298
_cell_measurement_temperature    100.1
_cell_measurement_theta_max      68.2
_cell_measurement_theta_min      4.1
_cell_volume                     596.23(13)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       'PROCESS-AUTO (Rigaku, 1998)'
_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_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID Imaging Plate'
_diffrn_measurement_method       '48 frames, δ ω = 15°'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5419
_diffrn_reflns_av_R_equivalents  0.109
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6375
_diffrn_reflns_theta_full        68.20
_diffrn_reflns_theta_max         68.20
_exptl_absorpt_coefficient_mu    0.921
_exptl_absorpt_correction_T_max  0.982
_exptl_absorpt_correction_T_min  0.896
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(ABSCOR; Higashi, 1995)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.617
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             300.00
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.25
_refine_diff_density_min         -0.30
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_parameters     105
_refine_ls_number_reflns         1097
_refine_ls_R_factor_gt           0.0680
_refine_ls_shift/su_max          0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0947P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.2134
_reflns_number_gt                520
_reflns_number_total             1097
_reflns_threshold_expression     F²>2σ(F²)
_cod_data_source_file            ob6597.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2207845
_cod_database_fobs_code          2207845
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_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_type_symbol
O1 0.9707(8) 0.53957(18) 0.7393(2) 0.0446(9) Uani d . 1.00 O
N1 0.7172(10) 0.4109(2) 0.6433(3) 0.0407(10) Uani d . 1.00 N
N2 0.1158(11) 0.1880(2) 0.3538(3) 0.0422(10) Uani d . 1.00 N
C1 0.5818(12) 0.5369(2) 0.5340(3) 0.0387(11) Uani d . 1.00 C
C2 0.7810(13) 0.5033(2) 0.6503(3) 0.0392(12) Uani d . 1.00 C
C3 0.5027(13) 0.3863(2) 0.5322(3) 0.0351(11) Uani d . 1.00 C
C4 0.4115(13) 0.2931(2) 0.5045(3) 0.0372(11) Uani d . 1.00 C
C5 0.5168(12) 0.2234(2) 0.5861(4) 0.0408(12) Uani d . 1.00 C
C6 0.4220(13) 0.1375(2) 0.5514(3) 0.0419(12) Uani d . 1.00 C
C7 0.2236(13) 0.1226(2) 0.4355(3) 0.0402(12) Uani d . 1.00 C
C8 0.2078(13) 0.2722(2) 0.3887(3) 0.0421(12) Uani d . 1.00 C
H1N 0.844(12) 0.369(2) 0.710(4) 0.064(15) Uiso d . 1.00 H
H5 0.6532 0.2352 0.6652 0.049 Uiso c R 1.00 H
H6 0.4915 0.0892 0.6060 0.050 Uiso c R 1.00 H
H7 0.1598 0.0630 0.4123 0.048 Uiso c R 1.00 H
H8 0.1319 0.3193 0.3328 0.050 Uiso c R 1.00 H
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
O1 0.062(2) 0.0398(18) 0.0270(16) -0.0020(16) -0.0097(15) -0.0034(14)
N1 0.056(2) 0.033(2) 0.028(2) -0.0001(19) -0.0102(18) -0.0012(17)
N2 0.053(2) 0.039(2) 0.031(2) 0.0013(19) -0.0041(18) 0.0028(17)
C1 0.053(3) 0.034(2) 0.026(2) -0.003(2) -0.004(2) 0.0023(18)
C2 0.050(3) 0.037(2) 0.029(2) -0.001(2) 0.001(2) -0.005(2)
C3 0.043(2) 0.035(2) 0.025(2) -0.002(2) -0.0019(19) -0.0001(18)
C4 0.040(3) 0.036(2) 0.032(2) 0.003(2) -0.006(2) 0.002(2)
C5 0.049(3) 0.037(2) 0.033(2) 0.004(2) -0.008(2) -0.002(2)
C6 0.059(3) 0.037(2) 0.028(2) 0.001(2) -0.002(2) 0.0062(19)
C7 0.057(3) 0.034(2) 0.026(2) 0.001(2) -0.006(2) 0.0010(19)
C8 0.056(3) 0.039(2) 0.028(2) -0.003(2) -0.007(2) 0.001(2)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.018 0.009
;
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 0.031 0.018
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.049 0.032
;
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
C2 N1 C3 . . 112.1(3) yes
C2 N1 H1N . . 121(2) no
C3 N1 H1N . . 126(2) no
C7 N2 C8 . . 117.3(3) no
C1 C1 C2 3_666 . 107.7(3) yes
C1 C1 C3 3_666 3_666 109.6(3) yes
C2 C1 C3 . 3_666 142.7(3) yes
O1 C2 N1 . . 123.2(3) yes
O1 C2 C1 . . 133.2(4) yes
N1 C2 C1 . . 103.7(3) yes
N1 C3 C1 . 3_666 106.9(3) yes
N1 C3 C4 . . 121.1(3) yes
C1 C3 C4 3_666 . 132.0(3) yes
C3 C4 C5 . . 123.6(3) yes
C3 C4 C8 . . 118.3(3) yes
C5 C4 C8 . . 118.0(3) no
C4 C5 C6 . . 119.5(3) no
C4 C5 H5 . . 120.2 no
C6 C5 H5 . . 120.2 no
C5 C6 C7 . . 118.8(3) no
C5 C6 H6 . . 120.6 no
C7 C6 H6 . . 120.6 no
N2 C7 C6 . . 123.6(3) no
N2 C7 H7 . . 118.2 no
C6 C7 H7 . . 118.2 no
N2 C8 C4 . . 122.7(3) no
N2 C8 H8 . . 118.6 no
C4 C8 H8 . . 118.6 no
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 C2 . 1.235(4) yes
N1 C2 . 1.406(5) yes
N1 C3 . 1.396(5) yes
N1 H1N . 1.02(4) no
N2 C7 . 1.347(5) no
N2 C8 . 1.348(5) no
C1 C1 3_666 1.417(5) yes
C1 C2 . 1.460(5) yes
C1 C3 3_666 1.372(5) yes
C3 C4 . 1.459(5) yes
C4 C5 . 1.392(5) no
C4 C8 . 1.407(5) no
C5 C6 . 1.374(5) no
C5 H5 . 0.950 no
C6 C7 . 1.383(5) no
C6 H6 . 0.950 no
C7 H7 . 0.950 no
C8 H8 . 0.950 no
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
_geom_hbond_publ_flag
N1 H1N N2 4_655 1.02(4) 1.93(4) 2.939(4) 168(3) yes
