#------------------------------------------------------------------------------ #$Date: 2012-02-03 17:16:24 +0000 (Fri, 03 Feb 2012) $ #$Revision: 32112 $ #$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_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 \q/2\q _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 'not determined' _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/[\s^2^(Fo^2^)+(0.0496P)^2^+0.2482P] where P = (Fo^2^+2Fc^2^)/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 \s(I)' _[local]_cod_data_source_file sk1568.cif _[local]_cod_data_source_block II _[local]_cod_cif_authors_sg_H-M 'P 21/c' _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 ; _cod_database_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_ _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_ _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_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