#------------------------------------------------------------------------------ #$Date: 2025-08-19 19:55:00 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301808 $ #$URL: svn://www.crystallography.net/cod/cif/2/30/00/2300017.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_2300017 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 116.6390(10) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 11.7973(4) _cell_length_b 8.1492(3) _cell_length_c 13.0286(3) _cell_measurement_reflns_used 2642 _cell_measurement_temperature 200.0(10) _cell_volume 1119.59(6) _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 200.0(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 0.0310 _diffrn_reflns_av_sigmaI/netI 0.0355 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_h_min -15 _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 3797 _diffrn_reflns_theta_max 28.26 _diffrn_reflns_theta_min 3.16 _exptl_absorpt_coefficient_mu 0.180 _exptl_absorpt_correction_T_max 0.990296 _exptl_absorpt_correction_T_min 0.518666 _exptl_absorpt_correction_type 'Empirical :Multipole Expansion' _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.870 _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 0.279 _refine_diff_density_min -0.294 _refine_ls_extinction_coef 0.0053(16) _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 1.084 _refine_ls_goodness_of_fit_obs 1.129 _refine_ls_matrix_type full _refine_ls_number_parameters 115 _refine_ls_number_reflns 1396 _refine_ls_number_restraints 5 _refine_ls_restrained_S_all 1.088 _refine_ls_restrained_S_obs 1.134 _refine_ls_R_factor_all 0.0535 _refine_ls_R_factor_obs 0.0421 _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^)+(0.0712P)^2^+0.6555P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_all 0.1267 _refine_ls_wR_factor_obs 0.1190 _reflns_number_observed 1154 _reflns_number_total 1396 _reflns_observed_criterion >2sigma(I) _cod_data_source_file do0021.cif _cod_data_source_block II200K _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^)+(0.0712P)^2^+0.6555P] 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^)+(0.0712P)^2^+0.6555P] 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 2300017 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 0.0186(7) 0.0164(7) 0.0165(6) 0.0014(5) 0.0085(5) 0.0016(5) N1 0.0427(12) 0.0116(9) 0.0365(11) 0.000 0.0310(10) 0.000 N2 0.0274(7) 0.0173(7) 0.0249(7) -0.0023(5) 0.0173(6) -0.0044(5) N3 0.0252(7) 0.0184(7) 0.0269(7) -0.0053(5) 0.0156(6) -0.0060(5) N4 0.0197(6) 0.0175(7) 0.0233(7) -0.0029(5) 0.0092(5) 0.0005(5) N5 0.0307(7) 0.0156(7) 0.0219(7) -0.0044(5) 0.0143(6) -0.0008(5) N6 0.0225(7) 0.0207(7) 0.0209(6) -0.0044(5) 0.0100(5) -0.0009(5) O1 0.0607(10) 0.0330(8) 0.0203(6) -0.0068(6) 0.0186(6) 0.0013(5) O2 0.0307(7) 0.0179(6) 0.0352(7) -0.0019(5) 0.0171(5) -0.0035(4) O3 0.0402(7) 0.0219(6) 0.0338(7) -0.0105(5) 0.0202(6) 0.0024(5) O4 0.0410(7) 0.0266(7) 0.0361(7) -0.0047(5) 0.0241(6) -0.0100(5) 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 0.42418(14) 0.4042(2) 0.29208(12) 0.0169(3) Uani d . 1 . C N1 0.5000 0.4753(2) 0.2500 0.0253(5) Uani d SD 1 . N N2 0.39127(13) 0.4986(2) 0.35646(11) 0.0211(3) Uani d D 1 . N N3 0.38439(13) 0.2522(2) 0.26813(12) 0.0220(3) Uani d D 1 . N N4 0.37453(12) 0.1479(2) 0.59967(11) 0.0203(3) Uani d . 1 . N N5 0.35415(14) -0.0164(2) 0.58702(11) 0.0218(3) Uani d . 1 . N N6 0.35698(12) -0.0869(2) 0.49049(11) 0.0213(3) Uani d . 1 . N O1 0.34102(15) -0.0115(2) 0.40423(10) 0.0378(4) Uani d . 1 . O O2 0.37056(11) -0.23684(14) 0.50053(10) 0.0271(3) Uani d . 1 . O O3 0.40996(13) 0.23445(15) 0.54201(11) 0.0306(3) Uani d . 1 . O O4 0.35823(13) 0.2035(2) 0.68118(11) 0.0320(3) Uani d . 1 . O H1 0.5000 0.5981(13) 0.2500 0.058(10) Uiso d SD 1 . H H2A 0.432(2) 0.6069(16) 0.3850(18) 0.042(6) Uiso d D 1 . H H2B 0.3234(16) 0.465(3) 0.3774(19) 0.044(6) Uiso d D 1 . H H3A 0.341(2) 0.203(3) 0.3109(17) 0.046(6) Uiso d D 1 . H H3B 0.392(2) 0.187(2) 0.2079(14) 0.038(6) 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_3 _geom_angle N3 C1 N2 . 121.76(14) N3 C1 N1 . 122.20(14) N2 C1 N1 . 116.03(14) C1 N1 C1 2_655 129.9(2) O3 N4 O4 . 122.38(14) O3 N4 N5 . 125.50(13) O4 N4 N5 . 112.06(12) N4 N5 N6 . 116.16(12) O1 N6 O2 . 123.85(14) O1 N6 N5 . 124.48(14) O2 N6 N5 . 111.55(12) 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 . 1.311(2) ? C1 N2 . 1.319(2) ? C1 N1 . 1.370(2) ? N1 C1 2_655 1.370(2) ? N4 O3 . 1.232(2) ? N4 O4 . 1.246(2) ? N4 N5 . 1.357(2) ? N5 N6 . 1.397(2) ? N6 O1 . 1.219(2) ? N6 O2 . 1.232(2) ? loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 PubChem 139063354