#------------------------------------------------------------------------------ #$Date: 2013-12-28 13:58:47 +0000 (Sat, 28 Dec 2013) $ #$Revision: 91933 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/22/2202232.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_2202232 loop_ _publ_author_name 'Zhu, Miaoli' 'Lu, Liping' 'Yang, Pin' _publ_section_title ; N,N-Dimethylbiguanidium nitrate ; _journal_issue 4 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o586 _journal_page_last o588 _journal_volume 59 _journal_year 2003 _chemical_formula_iupac 'C4 H12 N5 1+, N O3 1-' _chemical_formula_moiety 'C4 H12 N5 1+, N O3 1-' _chemical_formula_sum 'C4 H12 N6 O3' _chemical_formula_weight 192.20 _chemical_name_common 'N,N-dimethylbiguanidium nitrate' _chemical_name_systematic ; N,N-dimethylbiguanidium nitrate ; _space_group_IT_number 2 _symmetry_cell_setting triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 78.109(5) _cell_angle_beta 73.979(6) _cell_angle_gamma 85.353(6) _cell_formula_units_Z 2 _cell_length_a 7.204(3) _cell_length_b 7.534(3) _cell_length_c 8.821(4) _cell_measurement_reflns_used 2484 _cell_measurement_temperature 184(2) _cell_measurement_theta_max 24.727 _cell_measurement_theta_min 2.764 _cell_volume 450.1(3) _computing_cell_refinement SMART _computing_data_collection 'SMART (Bruker, 2000)' _computing_data_reduction 'SAINT (Bruker, 2000)' _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _computing_structure_refinement SHELXTL _computing_structure_solution 'SHELXTL (Sheldrick, 2000)' _diffrn_ambient_temperature 184(2) _diffrn_measured_fraction_theta_full 0.980 _diffrn_measured_fraction_theta_max 0.980 _diffrn_measurement_device_type 'Bruker SMART 1K CCD area-detector' _diffrn_measurement_method \w _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 0.0222 _diffrn_reflns_av_sigmaI/netI 0.0537 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_number 1875 _diffrn_reflns_theta_full 24.99 _diffrn_reflns_theta_max 24.99 _diffrn_reflns_theta_min 2.45 _diffrn_standards_decay_% 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.119 _exptl_absorpt_correction_T_max 0.9882 _exptl_absorpt_correction_T_min 0.9651 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 2000)' _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.418 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 204 _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _refine_diff_density_max 0.272 _refine_diff_density_min -0.200 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.011 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 155 _refine_ls_number_reflns 1559 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.011 _refine_ls_R_factor_all 0.0739 _refine_ls_R_factor_gt 0.0543 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0627P)^2^] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1186 _refine_ls_wR_factor_ref 0.1288 _reflns_number_gt 1181 _reflns_number_total 1559 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file ww6070.cif _[local]_cod_data_source_block I _cod_database_code 2202232 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol C1 0.3203(3) 0.1619(3) 0.7195(3) 0.0232(6) Uani d . 1 . . C C2 0.3318(4) 0.2505(3) 0.9550(3) 0.0236(6) Uani d . 1 . . C C3 0.2488(5) 0.0584(4) 0.4995(3) 0.0315(7) Uani d . 1 . . C C4 0.1365(6) -0.1112(4) 0.7791(4) 0.0477(9) Uani d . 1 . . C N1 0.2468(3) 0.0374(3) 0.6676(2) 0.0251(5) Uani d . 1 . . N N2 0.3802(3) 0.3163(3) 0.6177(3) 0.0290(6) Uani d . 1 . . N N3 0.3490(3) 0.1233(2) 0.8670(2) 0.0262(5) Uani d . 1 . . N N4 0.2262(3) 0.4036(3) 0.9364(3) 0.0309(6) Uani d . 1 . . N N5 0.4182(3) 0.2203(3) 1.0727(3) 0.0342(6) Uani d . 1 . . N N6 0.1893(3) 0.5910(3) 0.3001(3) 0.0316(6) Uani d . 1 . . N O1 0.3340(3) 0.4826(2) 0.2927(2) 0.0312(5) Uani d . 1 . . O O2 0.1352(3) 0.6691(3) 0.4143(3) 0.0542(6) Uani d . 1 . . O O3 0.1053(3) 0.6168(3) 0.1917(2) 0.0534(6) Uani d . 1 . . O H21 0.347(4) 0.357(4) 0.529(4) 0.051(3) Uiso d . 1 . . H H22 0.451(4) 0.388(4) 0.646(3) 0.051(3) Uiso d . 1 . . H H41 0.219(4) 0.468(4) 1.005(4) 0.051(3) Uiso d . 1 . . H H42 0.151(5) 0.418(4) 0.868(4) 0.051(3) Uiso d . 1 . . H H51 0.499(4) 0.123(4) 1.084(3) 0.051(3) Uiso d . 1 . . H H52 0.401(4) 0.294(4) 1.138(4) 0.051(3) Uiso d . 1 . . H H3A 0.368(5) 0.110(4) 0.435(4) 0.051(3) Uiso d . 1 . . H H4A 0.006(5) -0.095(4) 0.782(4) 0.051(3) Uiso d . 1 . . H H3B 0.147(4) 0.141(4) 0.472(3) 0.051(3) Uiso d . 1 . . H H4B 0.170(4) -0.224(4) 0.745(3) 0.051(3) Uiso d . 1 . . H H3C 0.231(4) -0.060(4) 0.476(3) 0.051(3) Uiso d . 1 . . H H4C 0.146(4) -0.119(4) 0.885(4) 0.051(3) Uiso d . 1 . . H 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 0.0173(13) 0.0265(13) 0.0250(13) 0.0027(11) -0.0048(11) -0.0056(10) C2 0.0249(14) 0.0258(13) 0.0191(12) -0.0013(11) -0.0055(11) -0.0025(10) C3 0.0318(17) 0.0356(16) 0.0318(15) 0.0009(13) -0.0132(13) -0.0113(12) C4 0.065(2) 0.0401(18) 0.0394(18) -0.0224(18) -0.0158(18) -0.0008(14) N1 0.0258(12) 0.0255(11) 0.0256(11) -0.0022(9) -0.0083(9) -0.0059(9) N2 0.0345(14) 0.0287(12) 0.0260(12) -0.0060(10) -0.0142(11) -0.0001(9) N3 0.0320(13) 0.0250(11) 0.0242(11) 0.0030(9) -0.0126(10) -0.0052(8) N4 0.0342(14) 0.0313(13) 0.0323(13) 0.0088(10) -0.0159(11) -0.0118(10) N5 0.0455(16) 0.0329(13) 0.0322(13) 0.0131(11) -0.0219(12) -0.0141(10) N6 0.0275(13) 0.0372(13) 0.0345(13) 0.0011(11) -0.0112(11) -0.0135(10) O1 0.0291(10) 0.0319(10) 0.0367(11) 0.0084(8) -0.0137(8) -0.0126(8) O2 0.0514(14) 0.0640(14) 0.0607(14) 0.0165(11) -0.0200(12) -0.0422(12) O3 0.0410(13) 0.0811(16) 0.0530(13) 0.0201(11) -0.0317(11) -0.0286(11) 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 N1 . 1.327(3) y C1 N2 . 1.335(3) y C1 N3 . 1.343(3) y C2 N5 . 1.324(3) y C2 N3 . 1.331(3) y C2 N4 . 1.336(3) y C3 N1 . 1.455(3) ? C3 H3A . 0.95(3) ? C3 H3B . 0.98(3) ? C3 H3C . 0.98(3) ? C4 N1 . 1.453(4) ? C4 H4A . 0.93(3) ? C4 H4B . 0.95(3) ? C4 H4C . 0.95(3) ? N2 H21 . 0.87(3) ? N2 H22 . 0.89(3) ? N4 H41 . 0.84(3) ? N4 H42 . 0.90(3) ? N5 H51 . 0.91(3) ? N5 H52 . 0.85(3) ? N6 O2 . 1.226(3) ? N6 O3 . 1.241(3) ? N6 O1 . 1.266(3) ? 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 _geom_angle_publ_flag N1 C1 N2 118.7(2) y N1 C1 N3 119.4(2) y N2 C1 N3 121.6(2) y N5 C2 N3 118.1(2) y N5 C2 N4 117.8(2) y N3 C2 N4 124.1(2) y N1 C3 H3A 108.3(17) ? N1 C3 H3B 112.5(17) ? H3A C3 H3B 107(2) ? N1 C3 H3C 109.4(16) ? H3A C3 H3C 112(2) ? H3B C3 H3C 108(2) ? N1 C4 H4A 110.5(19) ? N1 C4 H4B 112.4(18) ? H4A C4 H4B 103(3) ? N1 C4 H4C 111.9(17) ? H4A C4 H4C 107(3) ? H4B C4 H4C 111(2) ? C1 N1 C4 121.3(2) y C1 N1 C3 121.2(2) y C4 N1 C3 116.8(2) ? C1 N2 H21 125.2(19) ? C1 N2 H22 118.1(19) ? H21 N2 H22 117(3) ? C2 N3 C1 121.5(2) y C2 N4 H41 115(2) ? C2 N4 H42 118.8(18) ? H41 N4 H42 125(3) ? C2 N5 H51 120.1(18) ? C2 N5 H52 120(2) ? H51 N5 H52 119(3) ? O2 N6 O3 121.2(2) ? O2 N6 O1 119.2(2) ? O3 N6 O1 119.6(2) ? 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 _geom_hbond_publ_flag N5 H52 O1 1_556 0.85(3) 2.11(3) 2.962(3) 175(3) y N5 H51 N3 2_657 0.91(3) 2.10(3) 3.003(3) 171(3) y N4 H41 O3 1_556 0.84(3) 2.12(3) 2.932(3) 162(3) y N2 H21 O1 . 0.87(3) 2.13(3) 2.980(3) 166(3) y N2 H22 O1 2_666 0.89(3) 2.14(3) 3.009(3) 168(3) y N4 H42 O3 2_566 0.90(3) 2.10(3) 2.936(3) 153(3) y N4 H42 N2 . 0.90(3) 2.58(3) 2.913(3) 103(2) y loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_publ_flag N2 C1 N1 C4 -164.5(3) y N3 C1 N1 C4 21.6(4) y N2 C1 N1 C3 6.3(4) y N3 C1 N1 C3 -167.6(2) y N5 C2 N3 C1 -159.1(2) y N4 C2 N3 C1 23.8(4) y N1 C1 N3 C2 -147.5(2) y N2 C1 N3 C2 38.8(3) y _cod_database_fobs_code 2202232 _journal_paper_doi 10.1107/S1600536803006639