#------------------------------------------------------------------------------ #$Date: 2025-08-19 19:55:00 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301808 $ #$URL: svn://www.crystallography.net/cod/cif/2/30/00/2300016.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_2300016 loop_ _publ_author_name 'Bolotina, Nadezhda B.' 'Hardie, Michaele J.' 'Pinkerton, A. Alan' _publ_section_title ; Energetic materials: variable-temperature crystal structures of two biguanidinium dinitramides ; _journal_issue 6 _journal_name_full 'Journal of Applied Crystallography' _journal_page_first 1334 _journal_page_last 1341 _journal_paper_doi 10.1107/S0021889803016182 _journal_volume 36 _journal_year 2003 _chemical_formula_sum 'C2 H9 N11 O8' _chemical_formula_weight 315.20 _chemical_name_common 'biguanidinium bis-dinitramide' _space_group_IT_number 15 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-C 2yc' _symmetry_space_group_name_H-M 'C 1 2/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXTL _cell_angle_alpha 90.00 _cell_angle_beta 117.0050(10) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 11.7551(5) _cell_length_b 8.1557(3) _cell_length_c 13.0302(4) _cell_measurement_reflns_used 2658 _cell_measurement_temperature 150.0(10) _cell_measurement_theta_max 27.39 _cell_measurement_theta_min 4.02 _cell_volume 1113.01(7) _computing_cell_refinement 'Siemens SAINT, 1996b' _computing_data_collection 'Siemens SMART, 1996a' _computing_data_reduction 'Siemens SAINT, 1996b' _computing_molecular_graphics SHELXTL _computing_publication_material 'SHELXTL and the Toledo cifomatic' _computing_structure_refinement SHELXTL _computing_structure_solution 'SHELXTL (Sheldrick, 1997)' _diffrn_ambient_temperature 150.0(10) _diffrn_measurement_device Platform _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0289 _diffrn_reflns_av_sigmaI/netI 0.0339 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 3723 _diffrn_reflns_theta_max 28.26 _diffrn_reflns_theta_min 3.16 _exptl_absorpt_coefficient_mu 0.181 _exptl_absorpt_correction_T_max 0.990278 _exptl_absorpt_correction_T_min 0.759830 _exptl_absorpt_correction_type 'Empirical :Multipole Expansion' _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.881 _exptl_crystal_density_method '? ' _exptl_crystal_description block _exptl_crystal_F_000 648 _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.20 _refine_diff_density_max 0.277 _refine_diff_density_min -0.304 _refine_ls_extinction_coef 0.0052(13) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXTL _refine_ls_goodness_of_fit_all 1.051 _refine_ls_goodness_of_fit_obs 1.087 _refine_ls_matrix_type full _refine_ls_number_parameters 115 _refine_ls_number_reflns 1382 _refine_ls_number_restraints 5 _refine_ls_restrained_S_all 1.060 _refine_ls_restrained_S_obs 1.098 _refine_ls_R_factor_all 0.0455 _refine_ls_R_factor_obs 0.0371 _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/[\s^2^(Fo^2^)+(0.0578P)^2^+0.6566P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_all 0.1054 _refine_ls_wR_factor_obs 0.0995 _reflns_number_observed 1169 _reflns_number_total 1382 _reflns_observed_criterion >2sigma(I) _cod_data_source_file do0021.cif _cod_data_source_block II150K _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: '_refine_ls_weighting_scheme' value 'calc w=1/[\s^2^(Fo^2^)+(0.0578P)^2^+0.6566P] 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^)+(0.0578P)^2^+0.6566P] where P=(Fo^2^+2Fc^2^)/3'. Automatic conversion script Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas ; _cod_original_sg_symbol_H-M 'C 2/c' _cod_database_code 2300016 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -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 C1 0.0153(6) 0.0135(6) 0.0130(6) 0.0020(5) 0.0066(5) 0.0019(5) N1 0.0352(10) 0.0093(7) 0.0305(9) 0.000 0.0260(8) 0.000 N2 0.0218(6) 0.0138(6) 0.0197(6) -0.0017(4) 0.0136(5) -0.0029(4) N3 0.0207(6) 0.0144(6) 0.0212(6) -0.0038(4) 0.0124(5) -0.0047(4) N4 0.0163(5) 0.0147(6) 0.0174(5) -0.0017(4) 0.0074(4) 0.0006(4) N5 0.0259(6) 0.0121(6) 0.0183(6) -0.0033(4) 0.0128(5) -0.0007(4) N6 0.0182(6) 0.0159(6) 0.0163(5) -0.0031(4) 0.0079(4) -0.0008(4) O1 0.0455(7) 0.0257(6) 0.0158(5) -0.0045(5) 0.0146(5) 0.0020(4) O2 0.0251(5) 0.0135(5) 0.0264(5) -0.0015(4) 0.0134(4) -0.0024(4) O3 0.0314(6) 0.0172(5) 0.0261(5) -0.0079(4) 0.0158(5) 0.0018(4) O4 0.0326(6) 0.0212(6) 0.0269(6) -0.0029(4) 0.0188(5) -0.0075(4) 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 C1 0.42365(12) 0.4044(2) 0.29181(10) 0.0139(3) Uani d . 1 . C N1 0.5000 0.4754(2) 0.2500 0.0207(4) Uani d SD 1 . N N2 0.39051(11) 0.49880(13) 0.35611(10) 0.0168(3) Uani d D 1 . N N3 0.38360(11) 0.25225(14) 0.26764(10) 0.0176(3) Uani d D 1 . N N4 0.37457(10) 0.14795(14) 0.59952(9) 0.0162(3) Uani d . 1 . N N5 0.35450(12) -0.01672(14) 0.58695(10) 0.0177(3) Uani d . 1 . N N6 0.35794(10) -0.08732(14) 0.49061(9) 0.0167(3) Uani d . 1 . N O1 0.34253(12) -0.01174(13) 0.40410(9) 0.0287(3) Uani d . 1 . O O2 0.37074(10) -0.23752(12) 0.50055(9) 0.0210(3) Uani d . 1 . O O3 0.40975(11) 0.23485(12) 0.54175(9) 0.0238(3) Uani d . 1 . O O4 0.35779(10) 0.20320(13) 0.68102(9) 0.0249(3) Uani d . 1 . O H1 0.5000 0.5974(13) 0.2500 0.052(9) Uiso d SD 1 . H H2A 0.4296(18) 0.6069(15) 0.3841(16) 0.037(5) Uiso d D 1 . H H2B 0.3242(15) 0.464(2) 0.3783(16) 0.036(5) Uiso d D 1 . H H3A 0.3385(17) 0.206(2) 0.3089(15) 0.036(5) Uiso d D 1 . H H3B 0.3914(18) 0.188(2) 0.2077(12) 0.032(5) Uiso d D 1 . 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_ _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 N3 C1 N2 . 121.75(12) N3 C1 N1 . 122.12(12) N2 C1 N1 . 116.12(12) C1 N1 C1 2_655 130.0(2) O3 N4 O4 . 122.51(12) O3 N4 N5 . 125.55(11) O4 N4 N5 . 111.89(11) N4 N5 N6 . 116.13(10) O1 N6 O2 . 123.82(12) O1 N6 N5 . 124.54(12) O2 N6 N5 . 111.50(10) 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 C1 N3 . 1.314(2) ? C1 N2 . 1.320(2) ? C1 N1 . 1.3720(14) ? N1 C1 2_655 1.3720(14) ? N4 O3 . 1.2339(15) ? N4 O4 . 1.2490(15) ? N4 N5 . 1.361(2) ? N5 N6 . 1.3982(15) ? N6 O1 . 1.2240(14) ? N6 O2 . 1.234(2) ? loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 PubChem 139063354