#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/29/2012951.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_2012951
loop_
_publ_author_name
'Barnett, W. Mark'
'Baughman, Russell G.'
'Secondo, Paula M.'
'Hermansen, Charles J.'
_publ_section_title
;
 1,1'-Di(hydrazinocarbonylmethyl)-2,2'-biimidazole monohydrate and
 1,1'-di[2-(hydrazinocarbonyl)ethyl]-2,2'-biimidazole
;
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o565
_journal_page_last               o567
_journal_paper_doi               10.1107/S0108270102013458
_journal_volume                  58
_journal_year                    2002
_chemical_formula_iupac          'C12 H18 N8 O2'
_chemical_formula_moiety         'C12 H18 N8 O2'
_chemical_formula_sum            'C12 H18 N8 O2'
_chemical_formula_weight         306.33
_chemical_name_systematic
;
 1,1'-di(hydrazinopropanoyl)-2,2'-biimidazole
;
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 106.904(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.0505(5)
_cell_length_b                   4.9326(2)
_cell_length_c                   15.4663(7)
_cell_measurement_reflns_used    100
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      19.65
_cell_measurement_theta_min      7.72
_cell_volume                     733.61(6)
_computing_cell_refinement       'P3/P4-PC Diffractometer Program'
_computing_data_collection
'P3/P4-PC Diffractometer Program (Siemens, 1991)'
_computing_data_reduction        'XDISK (Siemens, 1991)'
_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      293(2)
_diffrn_measured_fraction_theta_full 0.99
_diffrn_measured_fraction_theta_max 0.99
_diffrn_measurement_device       'Siemens--Bruker P4'
_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  0.0257
_diffrn_reflns_av_sigmaI/netI    0.0272
_diffrn_reflns_limit_h_max       1
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       1
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            1899
_diffrn_reflns_theta_full        25.0
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         2.12
_diffrn_standards_decay_%        'ave. of 1.7 % in \s(I)s'
_diffrn_standards_interval_count 100
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_density_meas      ?
_exptl_crystal_description       'rectangular block'
_exptl_crystal_F_000             324
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.176
_refine_diff_density_min         -0.193
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.045
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     100
_refine_ls_number_reflns         1283
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_restrained_S_obs      1.084
_refine_ls_R_factor_all          0.0495
_refine_ls_R_factor_gt           0.0399
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0496P)²+0.2482P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1080
_refine_ls_wR_factor_ref         0.1009
_reflns_number_gt                1078
_reflns_number_total             1287
_reflns_threshold_expression     'I > 2 σ(I)'
_cod_data_source_file            sk1568.cif
_cod_data_source_block           II
_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 determined' 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 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2012951
_cod_database_fobs_code          2012951
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_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 0.0572(8) 0.0255(7) 0.0574(8) -0.0039(5) 0.0240(6) 0.0030(5)
N1 0.0434(8) 0.0360(8) 0.0413(8) -0.0038(6) 0.0193(6) -0.0002(6)
N2 0.0431(8) 0.0426(9) 0.0472(8) 0.0008(7) 0.0111(7) 0.0019(7)
N3 0.0506(9) 0.0278(8) 0.0577(9) -0.0011(7) 0.0211(7) 0.0014(7)
N4 0.0595(10) 0.0459(10) 0.0607(10) 0.0020(8) 0.0302(8) -0.0024(8)
C1 0.0390(9) 0.0311(9) 0.0400(8) 0.0003(7) 0.0168(7) -0.0024(7)
C2 0.0574(11) 0.0443(11) 0.0453(10) 0.0019(9) 0.0239(9) 0.0080(8)
C3 0.0541(11) 0.0514(12) 0.0432(10) 0.0065(9) 0.0130(8) 0.0052(9)
C4 0.0551(11) 0.0424(10) 0.0433(9) -0.0160(9) 0.0203(8) -0.0069(8)
C5 0.0428(10) 0.0393(10) 0.0464(10) -0.0074(8) 0.0073(8) 0.0069(8)
C6 0.0276(8) 0.0275(9) 0.0480(9) -0.0048(6) 0.0090(7) 0.0013(7)
loop_
_atom_site_label
_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_occupancy
_atom_site_disorder_group
_atom_site_type_symbol
O1 0.84779(13) 1.0937(2) 0.87916(9) 0.0451(4) Uani d . 1 . O
N1 0.56996(15) 0.7806(3) 0.94387(9) 0.0388(4) Uani d . 1 . N
N2 0.3743(2) 0.5492(3) 0.88759(10) 0.0447(4) Uani d . 1 . N
N3 0.8717(2) 0.6660(3) 0.83692(11) 0.0442(4) Uani d . 1 . N
H3A 0.8687(2) 0.4891(3) 0.85044(11) 0.080 Uiso d R 1 . H
N4 0.9002(2) 0.7358(3) 0.75521(12) 0.0526(4) Uani d . 1 . N
H4C 0.8281(2) 0.8303(3) 0.72000(12) 0.080 Uiso d R 1 . H
H4D 0.9776(2) 0.8382(3) 0.76777(12) 0.080 Uiso d R 1 . H
C1 0.4855(2) 0.5785(3) 0.95835(11) 0.0356(4) Uani d . 1 . C
C2 0.5070(2) 0.8814(4) 0.85903(12) 0.0471(5) Uani d . 1 . C
H2 0.5411(2) 1.0261(4) 0.82984(12) 0.080 Uiso d R 1 . H
C3 0.3888(2) 0.7385(4) 0.82599(13) 0.0498(5) Uani d . 1 . C
H3 0.3239(2) 0.7658(4) 0.76737(13) 0.080 Uiso d R 1 . H
C4 0.7041(2) 0.8773(4) 1.00172(12) 0.0457(5) Uani d . 1 . C
H4A 0.7096(2) 0.8431(4) 1.06378(12) 0.080 Uiso d R 1 . H
H4B 0.7105(2) 1.0695(4) 0.99418(12) 0.080 Uiso d R 1 . H
C5 0.8255(2) 0.7397(4) 0.97986(12) 0.0440(5) Uani d . 1 . C
H5A 0.8075(2) 0.5485(4) 0.97329(12) 0.080 Uiso d R 1 . H
H5B 0.9086(2) 0.7653(4) 1.02893(12) 0.080 Uiso d R 1 . H
C6 0.8484(2) 0.8480(3) 0.89408(11) 0.0348(4) Uani d . 1 . C
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
-3 -1 3
-2 0 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_3
_geom_angle
_geom_angle_publ_flag
C1 N1 C2 . 106.51(15) ?
C1 N1 C4 . 129.90(15) yes
C2 N1 C4 . 123.6(2) yes
C1 N2 C3 . 105.4(2) ?
C6 N3 N4 . 123.37(15) yes
C6 N3 H3A . 118.44 ?
N4 N3 H3A . 118.19 ?
N3 N4 H4C . 109.24 ?
N3 N4 H4D . 109.25 ?
H4C N4 H4D . 109.5 ?
N2 C1 N1 . 111.01(15) ?
N2 C1 C1 3_667 125.1(2) yes
N1 C1 C1 3_667 123.9(2) yes
C3 C2 N1 . 106.5(2) ?
C3 C2 H2 . 127.38 ?
N1 C2 H2 . 126.14 ?
C2 C3 N2 . 110.6(2) ?
C2 C3 H3 . 124.48 ?
N2 C3 H3 . 124.87 ?
N1 C4 C5 . 112.03(14) yes
N1 C4 H4A . 109.25 ?
C5 C4 H4A . 109.09 ?
N1 C4 H4B . 109.28 ?
C5 C4 H4B . 109.11 ?
H4A C4 H4B . 108.0 ?
C6 C5 C4 . 112.07(15) yes
C6 C5 H5A . 109.11 ?
C4 C5 H5A . 108.88 ?
C6 C5 H5B . 109.15 ?
C4 C5 H5B . 109.65 ?
H5A C5 H5B . 107.9 ?
O1 C6 N3 . 122.2(2) yes
O1 C6 C5 . 121.3(2) yes
N3 C6 C5 . 116.58(15) 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
O1 C6 . 1.233(2) yes
N1 C1 . 1.369(2) ?
N1 C2 . 1.374(2) ?
N1 C4 . 1.464(2) yes
N2 C1 . 1.325(2) ?
N2 C3 . 1.372(2) ?
N3 C6 . 1.328(2) yes
N3 N4 . 1.417(2) yes
N3 H3A . 0.90 ?
N4 H4C . 0.90 ?
N4 H4D . 0.90 ?
C1 C1 3_667 1.458(3) yes
C2 C3 . 1.348(3) ?
C2 H2 . 0.96 ?
C3 H3 . 0.96 ?
C4 C5 . 1.518(3) yes
C4 H4A . 0.96 ?
C4 H4B . 0.96 ?
C5 C6 . 1.509(2) yes
C5 H5A . 0.96 ?
C5 H5B . 0.96 ?
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
N4 H4C N2 2_656 0.90 2.47 3.367(2) 174
N4 H4D N4 2_756 0.90 2.40 3.213(2) 151
N3 H3A O1 1_545 0.90 2.03 2.923(2) 176
C3 H3 O1 2_646 0.96 2.56 3.441(2) 152
C4 H4A N2 3_667 0.96 2.32 2.960(2) 123
C4 H4B O1 . 0.96 2.55 2.900(2) 102
C5 H5B O1 3_777 0.96 2.54 3.471(2) 162
