#------------------------------------------------------------------------------ #$Date: 2025-08-19 07:12:48 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301798 $ #$URL: svn://www.crystallography.net/cod/cif/2/01/29/2012950.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_2012950 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 'C10 H14 N8 O2, H2 O' _chemical_formula_moiety 'C10 H14 N8 O2, H2 O' _chemical_formula_sum 'C10 H16 N8 O3' _chemical_formula_weight 296.29 _chemical_name_systematic ; 1,1'-di(hydrazinoethanoyl)2,2'-biimidazole monohydrate ; _space_group_IT_number 80 _symmetry_cell_setting tetragonal _symmetry_space_group_name_Hall 'I 4bw' _symmetry_space_group_name_H-M 'I 41' _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 90.00 _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 9.7451(3) _cell_length_b 9.7451(3) _cell_length_c 14.1764(6) _cell_measurement_reflns_used 100 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 19.68 _cell_measurement_theta_min 6.37 _cell_volume 1346.29(8) _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 0.0154 _diffrn_reflns_av_sigmaI/netI 0.0258 _diffrn_reflns_limit_h_max 1 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -1 _diffrn_reflns_limit_l_max 1 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 939 _diffrn_reflns_theta_full 25.0 _diffrn_reflns_theta_max 24.99 _diffrn_reflns_theta_min 2.54 _diffrn_standards_decay_% ; ave. in \s(I)'s of 1.7 ; _diffrn_standards_interval_count 100 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.113 _exptl_absorpt_correction_type none _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.462 _exptl_crystal_density_meas ? _exptl_crystal_description 'block cut from larger crystal' _exptl_crystal_F_000 624 _exptl_crystal_size_max 0.59 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.45 _refine_diff_density_max 0.136 _refine_diff_density_min -0.160 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_all 1.118 _refine_ls_goodness_of_fit_ref 1.139 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 99 _refine_ls_number_reflns 620 _refine_ls_number_restraints 3 _refine_ls_restrained_S_all 1.115 _refine_ls_restrained_S_obs 1.135 _refine_ls_R_factor_all 0.0370 _refine_ls_R_factor_gt 0.0316 _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^)+(0.0380P)^2^+0.5103P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_all 0.0798 _refine_ls_wR_factor_ref 0.0767 _reflns_number_gt 562 _reflns_number_total 620 _reflns_threshold_expression I>2\s(I) _cod_data_source_file sk1568.cif _cod_data_source_block I _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Tetragonal' changed to 'tetragonal' 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 'Tetragonal' changed to 'tetragonal' 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 ; _cod_original_cell_volume 1346.30(8) _cod_database_code 2012950 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' '-y, x+1/2, z+1/4' 'y+1/2, -x, z+3/4' 'x+1/2, y+1/2, z+1/2' '-x+1, -y+1, z+1' '-y+1/2, x+1, z+3/4' 'y+1, -x+1/2, z+5/4' 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 0.0381(11) 0.0450(13) 0.0321(11) 0.0104(9) 0.0037(10) 0.0089(10) O2 0.099(3) 0.058(2) 0.046(2) -0.025(2) 0.000 0.000 N1 0.0289(12) 0.0284(12) 0.0367(13) -0.0004(10) 0.0056(11) -0.0003(12) N2 0.0298(13) 0.0344(14) 0.054(2) 0.0040(10) 0.0030(13) -0.0013(14) N3 0.0335(13) 0.0349(14) 0.0331(12) 0.0082(11) 0.0011(11) 0.0030(11) N4 0.0372(14) 0.0402(15) 0.0430(15) 0.0095(10) 0.0067(13) -0.0004(13) C1 0.0301(14) 0.0284(14) 0.032(2) 0.0004(12) 0.0007(14) -0.0002(13) C2 0.0294(15) 0.041(2) 0.049(2) -0.0050(14) 0.0074(15) -0.005(2) C3 0.0250(14) 0.046(2) 0.063(2) -0.0011(14) 0.006(2) -0.005(2) C4 0.036(2) 0.0238(14) 0.036(2) 0.0007(11) 0.0063(15) 0.0053(13) C5 0.0276(14) 0.0228(15) 0.0324(15) -0.0033(11) 0.0004(13) 0.0030(12) 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 0.5130(2) 0.2547(2) 0.5599(2) 0.0384(5) Uani d . 1 . O O2 0.5000 0.0000 0.41219(13) 0.0676(13) Uani d SD 1 . O H2A 0.503(6) 0.0691(2) 0.3757(3) 0.080 Uiso d D 1 . H N1 0.4009(2) 0.3361(2) 0.7275(2) 0.0314(5) Uani d . 1 . N N2 0.3170(3) 0.5473(3) 0.7237(3) 0.0395(7) Uani d . 1 . N N3 0.6668(2) 0.1164(3) 0.6313(3) 0.0338(6) Uani d . 1 . N H3A 0.6945(2) 0.0809(3) 0.6870(3) 0.080 Uiso d R 1 . H N4 0.7422(3) 0.0819(3) 0.5499(2) 0.0402(6) Uani d . 1 . N H4D 0.6858(3) 0.0402(3) 0.5084(2) 0.080 Uiso d R 1 . H H4C 0.7767(3) 0.1584(3) 0.5234(2) 0.080 Uiso d R 1 . H C1 0.4306(3) 0.4728(3) 0.7275(3) 0.0302(6) Uani d . 1 . C C2 0.2607(3) 0.3242(3) 0.7222(3) 0.0397(7) Uani d . 1 . C H2 0.2071(3) 0.2414(3) 0.7198(3) 0.080 Uiso d R 1 . H C3 0.2128(3) 0.4538(4) 0.7201(3) 0.0448(8) Uani d . 1 . C H3 0.1173(3) 0.4782(4) 0.7174(3) 0.080 Uiso d R 1 . H C4 0.4940(3) 0.2194(3) 0.7275(3) 0.0320(7) Uani d . 1 . C H4A 0.4453(3) 0.1374(3) 0.7450(3) 0.080 Uiso d R 1 . H H4B 0.5650(3) 0.2348(3) 0.7735(3) 0.080 Uiso d R 1 . H C5 0.5589(3) 0.2002(3) 0.6308(3) 0.0276(6) 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 0 1 -5 1 0 -5 -2 1 -3 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 . 107.1(2) ? C1 N1 C4 . 129.2(2) yes C2 N1 C4 . 123.7(3) yes C1 N2 C3 . 104.9(3) ? C5 N3 N4 . 123.6(3) yes C5 N3 H3A . 118.4 ? N4 N3 H3A . 117.96 ? N3 N4 H4D . 108.9 ? N3 N4 H4C . 109.8 ? H4D N4 H4C . 109.2 ? N2 C1 N1 . 111.0(2) ? N2 C1 C1 6_554 125.3(3) yes N1 C1 C1 6_554 123.6(3) yes C3 C2 N1 . 105.5(3) ? C3 C2 H2 . 126.7 ? N1 C2 H2 . 127.8 ? C2 C3 N2 . 111.6(3) ? C2 C3 H3 . 124.7 ? N2 C3 H3 . 123.8 ? N1 C4 C5 . 110.8(2) yes N1 C4 H4A . 109.98 ? C5 C4 H4A . 109.65 ? N1 C4 H4B . 109.1 ? C5 C4 H4B . 109.33 ? H4A C4 H4B . 108.0 ? O1 C5 N3 . 124.0(3) yes O1 C5 C4 . 122.4(2) yes N3 C5 C4 . 113.5(3) yes H4D O2 H2A . 102 yes H4D O2 H2A 6_544 122 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 C5 . 1.222(4) yes O2 H2A . 0.850(5) ? N1 C1 . 1.364(4) ? N1 C2 . 1.374(4) ? N1 C4 . 1.455(3) yes N2 C1 . 1.325(4) ? N2 C3 . 1.366(4) ? N3 C5 . 1.331(4) yes N3 N4 . 1.410(4) yes N3 H3A . 0.90 ? N4 H4D . 0.90 ? N4 H4C . 0.90 ? C1 C1 6_554 1.453(5) yes C2 C3 . 1.346(5) ? C2 H2 . 0.96 ? C3 H3 . 0.96 ? C4 C5 . 1.521(4) yes C4 H4A . 0.96 ? C4 H4B . 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 O2 H2a N4 4_564 0.850(5) 2.27(2) 3.080(3) 161(4) N3 H3a O1 3_645 0.90 1.93 2.830(3) 176 N4 H4c N2 7_644 0.90 2.41 3.260(4) 157 N4 H4d O2 . 0.90 2.30 3.165(4) 161 loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 PubChem 139058665