#------------------------------------------------------------------------------
#$Date: 2016-02-19 16:29:56 +0200 (Fri, 19 Feb 2016) $
#$Revision: 176759 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/54/2005499.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_2005499
loop_
_publ_author_name
'Secondo, P. M.'
'Barnett, W. M.'
'Collier, H. L.'
'Baughman, R. G.'
_publ_section_title
;
 1,1'-Diketone and 1,1'-Dinitrile Derivatives of 2,2'-Biimidazole
;
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              2636
_journal_page_last               2638
_journal_paper_doi               10.1107/S0108270196005823
_journal_volume                  52
_journal_year                    1996
_chemical_formula_moiety         'C12 H14 N4 O2'
_chemical_formula_sum            'C6 H7 N2 O'
_chemical_formula_weight         246.3
_chemical_name_systematic
;
1,1'-di(2-propanone)-2,2'-biimidazole
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 110.744(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.1649(9)
_cell_length_b                   8.6999(13)
_cell_length_c                   8.9848(11)
_cell_measurement_reflns_used    50
_cell_measurement_temperature    288(2)
_cell_measurement_theta_max      20.65
_cell_measurement_theta_min      6.61
_cell_volume                     596.85(14)
_computing_cell_refinement       'P3/P4-PC Diffractometer Program'
_computing_data_collection
'P3/P4-PC Diffractometer Program (Siemens, 1991a)'
_computing_data_reduction        'XDISK (Siemens, 1991b)'
_computing_molecular_graphics    'SHELXTL/PC (Sheldrick, 1990b)'
_computing_publication_material  'SHELXTL/PC and SHELXL93'
_computing_structure_refinement  'SHELXL93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS86 (Sheldrick, 1990a)'
_diffrn_ambient_temperature      288(2)
_diffrn_measurement_device       'Siemens P3 diffractometer'
_diffrn_measurement_method       θ/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0117
_diffrn_reflns_av_sigmaI/netI    0.0158
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -2
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -2
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            1842
_diffrn_reflns_theta_max         25.05
_diffrn_reflns_theta_min         2.90
_diffrn_standards_decay_%        'ave. of 1.5% in \s(I)'s'
_diffrn_standards_interval_count 50
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.370
_exptl_crystal_density_meas      ?
_exptl_crystal_description       'block cut from prism'
_exptl_crystal_F_000             260
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.210
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.146
_refine_ls_goodness_of_fit_obs   1.200
_refine_ls_hydrogen_treatment    'H atoms riding, C-H 0.96\%A'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     82
_refine_ls_number_reflns         1047
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.158
_refine_ls_restrained_S_obs      1.200
_refine_ls_R_factor_all          0.0521
_refine_ls_R_factor_obs          0.0435
_refine_ls_shift/esd_max         0.000
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0692P)²+0.2406P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1401
_refine_ls_wR_factor_obs         0.1330
_reflns_number_observed          895
_reflns_number_total             1053
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            fg1166.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 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' 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 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc w =
1/[\s^2^(Fo^2^)+(0.0692P)^2^+0.2406P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to 'w =
1/[\s^2^(Fo^2^)+(0.0692P)^2^+0.2406P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        596.85(13)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2005499
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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
O 0.0479(10) 0.0662(11) 0.0450(9) -0.0055(8) 0.0037(7) 0.0096(8)
N1 0.0409(10) 0.0392(10) 0.0366(9) -0.0023(7) 0.0107(7) -0.0008(7)
N2 0.0394(10) 0.0460(10) 0.0516(10) -0.0038(8) 0.0169(8) 0.0002(8)
C1 0.0368(10) 0.0356(11) 0.0343(10) -0.0019(9) 0.0090(8) 0.0027(8)
C2 0.0518(13) 0.0475(13) 0.0486(12) 0.0057(11) 0.0216(10) -0.0016(10)
C3 0.0449(12) 0.0535(14) 0.0603(14) 0.0019(11) 0.0255(11) 0.0010(11)
C4 0.0448(11) 0.0433(11) 0.0362(10) -0.0071(10) 0.0064(9) -0.0055(9)
C5 0.0414(11) 0.0346(11) 0.0418(11) -0.0008(9) 0.0106(9) -0.0050(8)
C6 0.0517(14) 0.062(2) 0.0553(14) -0.0150(12) 0.0123(11) -0.0028(12)
loop_
_atom_site_label
_atom_site_occupancy
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_type_symbol
O 1 -0.0384(2) 0.1411(2) 0.6075(2) 0.0565(5) Uani d . O
N1 1 0.0224(2) 0.3281(2) 0.3837(2) 0.0397(5) Uani d . N
N2 1 0.2191(2) 0.5125(2) 0.4845(2) 0.0455(5) Uani d . N
C1 1 0.0606(3) 0.4619(2) 0.4688(2) 0.0365(5) Uani d . C
C2 1 0.1659(3) 0.2938(3) 0.3451(3) 0.0483(6) Uani d . C
H2B 1 0.1799(3) 0.2064(3) 0.2855(3) 0.080 Uiso d R H
C3 1 0.2838(3) 0.4070(3) 0.4066(3) 0.0510(6) Uani d . C
H3A 1 0.3995(3) 0.4102(3) 0.4023(3) 0.080 Uiso d R H
C4 1 -0.1351(3) 0.2357(3) 0.3418(2) 0.0436(5) Uani d . C
H4A 1 -0.1346(3) 0.1620(3) 0.2625(2) 0.080 Uiso d R H
H4B 1 -0.2330(3) 0.3030(3) 0.2949(2) 0.080 Uiso d R H
C5 1 -0.1571(3) 0.1534(2) 0.4804(2) 0.0403(5) Uani d . C
C6 1 -0.3326(3) 0.0849(3) 0.4484(3) 0.0580(7) Uani d . C
H6A 1 -0.3356(3) 0.0345(3) 0.5425(3) 0.080 Uiso d R H
H6B 1 -0.4197(3) 0.1645(3) 0.4179(3) 0.080 Uiso d R H
H6C 1 -0.3564(3) 0.0114(3) 0.3636(3) 0.080 Uiso d R 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_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
0 2 2
1 1 2
2 0 -2
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 N1 C2 . 106.3(2) yes
C1 N1 C4 . 128.6(2) yes
C2 N1 C4 . 125.1(2) yes
C1 N2 C3 . 105.1(2) yes
N2 C1 N1 . 111.3(2) yes
N2 C1 C1 3_566 125.3(2) yes
N1 C1 C1 3_566 123.4(2) yes
C3 C2 N1 . 106.7(2) yes
C2 C3 N2 . 110.5(2) yes
N1 C4 C5 . 113.9(2) yes
O C5 C6 . 122.8(2) yes
O C5 C4 . 122.2(2) yes
C6 C5 C4 . 115.0(2) yes
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
O C5 . 1.213(2) yes
N1 C1 . 1.367(3) yes
N1 C2 . 1.368(3) yes
N1 C4 . 1.449(3) yes
N2 C1 . 1.326(3) yes
N2 C3 . 1.369(3) yes
C1 C1 3_566 1.459(4) yes
C2 C3 . 1.351(3) yes
C4 C5 . 1.501(3) yes
C5 C6 . 1.483(3) yes
