#------------------------------------------------------------------------------
#$Date: 2016-02-14 16:26:36 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176435 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/28/2202809.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_2202809
loop_
_publ_author_name
'Mizuguchi, Jin'
_publ_section_title
;2,5-Dihydro-2,5-dimethyl-3,6-diphenylpyrrolo[3,4-c]pyrrole-1,4-(diylidene)bis(cyanamide)
 chloroform disolvate
;
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1453
_journal_page_last               o1454
_journal_paper_doi               10.1107/S1600536803019172
_journal_volume                  59
_journal_year                    2003
_chemical_formula_moiety         'C22 H16 N6 , 2C H Cl3'
_chemical_formula_sum            'C24 H18 Cl6 N6'
_chemical_formula_weight         603.16
_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
_cell_angle_beta                 110.61(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.656(3)
_cell_length_b                   13.768(7)
_cell_length_c                   11.670(5)
_cell_measurement_reflns_used    6142
_cell_measurement_temperature    93.2
_cell_measurement_theta_max      67.6
_cell_measurement_theta_min      4.0
_cell_volume                     1301.8(10)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_reduction
;
TEXSAN (Molecular Structure Corporation, 2001)
;
_computing_molecular_graphics    'ORTEP-III (Burnett & Johnson, 1996)'
_computing_publication_material  TEXSAN
_computing_structure_refinement  TEXSAN
_computing_structure_solution    'SHELXS86 (Sheldrick 1985)'
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.95
_diffrn_measured_fraction_theta_max 0.95
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID Imaging Plate'
_diffrn_measurement_method       '48 frames, delta omega = 15 deg'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.074
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            11504
_diffrn_reflns_theta_full        68.19
_diffrn_reflns_theta_max         68.19
_exptl_absorpt_coefficient_mu    6.245
_exptl_absorpt_correction_T_max  0.8830
_exptl_absorpt_correction_T_min  0.3960
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Higashi, 1995)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.539
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             612.0
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.48
_refine_diff_density_min         -0.42
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.289
_refine_ls_hydrogen_treatment    noref
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2235
_refine_ls_R_factor_gt           0.0435
_refine_ls_shift/su_max          0.0099
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²) + (0.05(Max(Fo²,0) + 2Fc²)/3)²]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1183
_reflns_number_gt                1924
_reflns_number_total             2361
_reflns_threshold_expression     F²>2σ(F²)
_cod_data_source_file            ob6291.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_original_formula_sum        'C24 H18 Cl6 N6 '
_cod_database_code               2202809
_cod_database_fobs_code          2202809
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,1/2+y,1/2-z
-x,-y,-z
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_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
Cl1 0.62330(8) 0.84981(4) 0.32331(6) 0.0335(2) Uani d . 1.00 . . Cl
Cl2 0.91335(9) 0.72697(5) 0.41190(7) 0.0395(2) Uani d . 1.00 . . Cl
Cl3 0.74563(9) 0.78599(5) 0.57591(6) 0.0340(2) Uani d . 1.00 . . Cl
N1 0.0940(3) 0.53110(10) -0.1411(2) 0.0227(5) Uani d . 1.00 . . N
N2 0.3306(2) 0.58370(10) 0.0148(2) 0.0240(5) Uani d . 1.00 . . N
N3 0.5220(3) 0.5981(2) 0.2302(2) 0.0300(6) Uani d . 1.00 . . N
C1 -0.1567(3) 0.4443(2) -0.2762(2) 0.0237(6) Uani d . 1.00 . . C
C2 -0.2096(3) 0.5004(2) -0.3846(2) 0.0266(7) Uani d . 1.00 . . C
C3 -0.3044(3) 0.4577(2) -0.4942(2) 0.0334(7) Uani d . 1.00 . . C
C4 -0.3464(3) 0.3599(2) -0.4984(2) 0.0313(7) Uani d . 1.00 . . C
C5 -0.2967(3) 0.3047(2) -0.3924(2) 0.0288(7) Uani d . 1.00 . . C
C6 -0.2025(3) 0.3467(2) -0.2816(2) 0.0246(6) Uani d . 1.00 . . C
C7 -0.0538(3) 0.4848(2) -0.1580(2) 0.0225(6) Uani d . 1.00 . . C
C8 0.1675(3) 0.5453(2) -0.2357(2) 0.0290(7) Uani d . 1.00 . . C
C9 0.1802(3) 0.5503(2) -0.0170(2) 0.0220(6) Uani d . 1.00 . . C
C10 -0.0713(3) 0.4795(2) -0.0450(2) 0.0227(6) Uani d . 1.00 . . C
C11 0.4256(3) 0.5906(2) 0.1321(2) 0.0229(6) Uani d . 1.00 . . C
C12 0.7205(3) 0.7540(2) 0.4239(2) 0.0274(7) Uani d . 1.00 . . C
H1 -0.1803 0.5672 -0.3821 0.0319 Uiso calc . 1.00 . . H
H2 -0.3408 0.4954 -0.5671 0.0401 Uiso calc . 1.00 . . H
H3 -0.4095 0.3307 -0.5744 0.0376 Uiso calc . 1.00 . . H
H4 -0.3271 0.2381 -0.3956 0.0346 Uiso calc . 1.00 . . H
H5 -0.1691 0.3088 -0.2089 0.0296 Uiso calc . 1.00 . . H
H6 0.2692 0.5793 -0.2016 0.0348 Uiso calc . 1.00 . . H
H7 0.0943 0.5820 -0.3013 0.0348 Uiso calc . 1.00 . . H
H8 0.1865 0.4839 -0.2653 0.0348 Uiso calc . 1.00 . . H
H9 0.6521 0.6978 0.4018 0.0329 Uiso calc . 1.00 . . H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.018 0.009
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
H H 0.000 0.000
;International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.2)
;
N N 0.031 0.018
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
Cl Cl 0.364 0.702
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
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 C8 . . 125.4(2) yes
C7 N1 C9 . . 111.3(2) yes
C8 N1 C9 . . 122.6(2) yes
C9 N2 C11 . . 120.7(2) yes
C2 C1 C6 . . 119.2(2) no
C2 C1 C7 . . 122.3(2) yes
C6 C1 C7 . . 118.4(2) yes
C1 C2 C3 . . 119.7(2) yes
C1 C2 H1 . . 120.1 no
C3 C2 H1 . . 120.1 no
C2 C3 C4 . . 120.3(2) no
C2 C3 H2 . . 119.9 no
C4 C3 H2 . . 119.8 no
C3 C4 C5 . . 120.3(2) no
C3 C4 H3 . . 119.8 no
C5 C4 H3 . . 119.8 no
C4 C5 C6 . . 120.0(2) no
C4 C5 H4 . . 120.0 no
C6 C5 H4 . . 120.0 no
C1 C6 C5 . . 120.4(2) no
C1 C6 H5 . . 119.8 no
C5 C6 H5 . . 119.8 no
N1 C7 C1 . . 122.3(2) yes
N1 C7 C10 . . 107.2(2) yes
C1 C7 C10 . . 130.2(2) yes
N1 C8 H6 . . 109.5 no
N1 C8 H7 . . 109.4 no
N1 C8 H8 . . 109.4 no
H6 C8 H7 . . 109.5 no
H6 C8 H8 . . 109.5 no
H7 C8 H8 . . 109.5 no
N1 C9 N2 . . 118.4(2) yes
N1 C9 C10 . 3_565 105.2(2) yes
N2 C9 C10 . 3_565 136.3(2) yes
C7 C10 C9 . 3_565 144.0(2) yes
C7 C10 C10 . 3_565 109.0(3) yes
C9 C10 C10 3_565 3_565 107.0(3) yes
N2 C11 N3 . . 172.9(3) yes
Cl1 C12 Cl2 . . 110.40(10) no
Cl1 C12 Cl3 . . 110.00(10) no
Cl1 C12 H9 . . 108.7 no
Cl2 C12 Cl3 . . 110.30(10) no
Cl2 C12 H9 . . 108.7 no
Cl3 C12 H9 . . 108.7 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C12 . . 1.771(3) no
Cl2 C12 . . 1.765(3) no
Cl3 C12 . . 1.765(3) no
N1 C7 . . 1.377(3) yes
N1 C8 . . 1.468(3) yes
N1 C9 . . 1.401(3) yes
N2 C9 . . 1.304(3) yes
N2 C11 . . 1.330(3) yes
N3 C11 . . 1.160(3) yes
C1 C2 . . 1.414(3) no
C1 C6 . . 1.395(3) no
C1 C7 . . 1.463(3) yes
C2 C3 . . 1.383(3) no
C2 H1 . . 0.950 no
C3 C4 . . 1.390(4) no
C3 H2 . . 0.950 no
C4 C5 . . 1.386(4) no
C4 H3 . . 0.950 no
C5 C6 . . 1.388(3) no
C5 H4 . . 0.951 no
C6 H5 . . 0.951 no
C7 C10 . . 1.381(3) yes
C8 H6 . . 0.950 no
C8 H7 . . 0.950 no
C8 H8 . . 0.950 no
C9 C10 . 3_565 1.434(3) yes
C10 C10 . 3_565 1.425(4) yes
C12 H9 . . 0.951 no
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
Cl1 C11 3.407(2) 2_655 no
Cl1 C10 3.466(3) 4_665 no
Cl1 C7 3.552(3) 4_665 no
Cl1 C9 3.594(3) 2_655 no
Cl2 C5 3.435(3) 3_665 no
Cl2 C6 3.508(3) 3_665 no
Cl3 N3 3.463(3) 4_565 no
Cl3 C11 3.503(3) 4_565 no
N2 C5 3.330(3) 2_554 no
N3 C12 3.148(3) . no
N3 C8 3.317(4) 3_665 no
N3 C3 3.598(3) 1_656 no
C3 C3 3.538(4) 3_464 no
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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
N1 C7 C1 C2 . . . -54.3(3) yes
N1 C7 C1 C6 . . . 125.2(3) yes
N1 C7 C10 C9 . . 3_565 176.5(3) no
N1 C7 C10 C10 . . 3_565 -1.9(3) no
N1 C9 N2 C11 . . . -170.7(2) yes
N1 C9 C10 C7 . 3_565 3_565 -178.2(3) no
N1 C9 C10 C10 . 3_565 . 3.4(3) no
N2 C9 N1 C7 . . . 172.3(2) no
N2 C9 N1 C8 . . . 1.2(3) no
N2 C9 C10 C7 . 3_565 3_565 5.6(6) yes
N2 C9 C10 C10 . 3_565 . -172.8(3) no
C1 C2 C3 C4 . . . -0.6(4) no
C1 C2 C3 H2 . . . 179.5 no
C1 C6 C5 C4 . . . -0.3(4) no
C1 C6 C5 H4 . . . 179.7 no
C1 C7 N1 C8 . . . -0.4(4) no
C1 C7 N1 C9 . . . -171.2(2) no
C1 C7 C10 C9 . . 3_565 -8.6(5) no
C1 C7 C10 C10 . . 3_565 173.0(2) no
C2 C1 C6 C5 . . . 1.1(4) no
C2 C1 C6 H5 . . . -178.9 no
C2 C1 C7 C10 . . . 131.5(3) no
C2 C3 C4 C5 . . . 1.4(4) no
C2 C3 C4 H3 . . . -178.6 no
C3 C2 C1 C6 . . . -0.6(4) no
C3 C2 C1 C7 . . . 178.9(3) no
C3 C4 C5 C6 . . . -0.9(4) no
C3 C4 C5 H4 . . . 179.1 no
C4 C3 C2 H1 . . . 179.5 no
C4 C5 C6 H5 . . . 179.7 no
C5 C4 C3 H2 . . . -178.7 no
C5 C6 C1 C7 . . . -178.4(2) no
C6 C1 C2 H1 . . . 179.3 no
C6 C1 C7 C10 . . . -49.0(4) no
C6 C5 C4 H3 . . . 179.1 no
C7 N1 C8 H6 . . . 179.8 no
C7 N1 C8 H7 . . . 59.8 no
C7 N1 C8 H8 . . . -60.1 no
C7 N1 C9 C10 . . 3_565 -4.8(2) no
C7 C1 C2 H1 . . . -1.2 no
C7 C1 C6 H5 . . . 1.6 no
C7 C10 C10 C7 . 3_565 3_565 -180.0 no
C7 C10 C10 C9 . 3_565 . -1.0(3) no
C8 N1 C7 C10 . . . 175.0(2) no
C8 N1 C9 C10 . . 3_565 -175.8(2) no
C9 N1 C7 C10 . . . 4.2(3) no
C9 N1 C8 H6 . . . -10.4 no
C9 N1 C8 H7 . . . -130.4 no
C9 N1 C8 H8 . . . 109.6 no
C9 C10 C10 C9 3_565 . 3_565 -180.0 no
C10 C9 N2 C11 3_565 3_565 3_565 -5.1(4) yes
H1 C2 C3 H2 . . . -0.5 no
H2 C3 C4 H3 . . . 1.3 no
H3 C4 C5 H4 . . . -0.9 no
H4 C5 C6 H5 . . . -0.3 no
H4 C5 C6 H5 . . . -0.3 no
