#------------------------------------------------------------------------------ #$Date: 2015-01-23 14:30:19 +0200 (Fri, 23 Jan 2015) $ #$Revision: 130086 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/00/83/2008333.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_2008333 loop_ _publ_author_name 'Zaleski, Jacek' 'Daszkiewicz, Zdzis\/law' 'Kyzio\/l, Janusz' _publ_section_title ; 1-Methyl-4-(N-methylnitramino)pyridinium bromide ; _journal_issue 4 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 691 _journal_page_last 693 _journal_paper_doi 10.1107/S0108270198014656 _journal_volume 55 _journal_year 1999 _chemical_formula_moiety 'C7 H10 N3 O2^+^.Br^-^' _chemical_formula_structural 'see form.eps' _chemical_formula_sum 'C7 H10 Br N3 O2' _chemical_formula_weight 248.09 _chemical_melting_point 425.15 _chemical_name_systematic ; '4--(N--Methylnitramino)-1--methylpyridinium bromide' ; _space_group_IT_number 61 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall '-P 2ac 2ab' _symmetry_space_group_name_H-M 'P b c a' _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_formula_units_Z 8 _cell_length_a 10.480(2) _cell_length_b 11.949(2) _cell_length_c 15.005(3) _cell_measurement_reflns_used 20 _cell_measurement_temperature 295(2) _cell_measurement_theta_max 15 _cell_measurement_theta_min 8 _cell_volume 1879.0(6) _computing_cell_refinement 'Kuma KM-4 Users Guide' _computing_data_collection 'Kuma KM-4 Users Guide (Kuma, 1997)' _computing_data_reduction 'Kuma KM-4 Users Guide' _computing_molecular_graphics SHELXTL-Plus _computing_publication_material SHELXL-97 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXTL-Plus (Sheldrick, 1990)' _diffrn_ambient_temperature 295(2) _diffrn_measured_fraction_theta_full 0.860 _diffrn_measured_fraction_theta_max 0.860 _diffrn_measurement_device_type 'Kuma KM-4' _diffrn_measurement_method \w-\q _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 0.0439 _diffrn_reflns_av_sigmaI/netI 0.0501 _diffrn_reflns_limit_h_max 0 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 0 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 3059 _diffrn_reflns_theta_full 25.07 _diffrn_reflns_theta_max 25.07 _diffrn_reflns_theta_min 2.92 _diffrn_standards_decay_% 0.72 _diffrn_standards_interval_count 50 _diffrn_standards_number 2 _exptl_absorpt_coefficient_mu 4.347 _exptl_absorpt_correction_T_max 0.647 _exptl_absorpt_correction_T_min 0.143 _exptl_absorpt_correction_type 'semiempirical from \y scan (SHELXTL, Sheldrick, 1990)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.754 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description plates _exptl_crystal_F_000 992 _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.1 _refine_diff_density_max 0.524 _refine_diff_density_min -0.261 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.000 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 158 _refine_ls_number_reflns 1639 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.000 _refine_ls_R_factor_all 0.0664 _refine_ls_R_factor_gt 0.0293 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_scheme 'calc w = 1/[\s^2^(Fo^2^)+(0.0426P)^2^+0.1823P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_wR_factor_ref 0.0823 _reflns_number_gt 1104 _reflns_number_total 1639 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file cf1290.cif _[local]_cod_data_source_block k1 _[local]_cod_cif_authors_sg_H-M Pbca _cod_depositor_comments ; The following automatic conversions were performed: '_chemical_melting_point' value '152 \%C' was changed to '425.15' - it was converted from degrees Celsius(C) to Kelvins(K). Automatic conversion script Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana The following automatic conversions were performed: '_chemical_melting_point' value '152 \%C' was changed to '425.15' - it was converted from degrees Celsius(C) to Kelvins(K). 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_database_code 2008333 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, 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 Br 0.18320(3) 0.81321(3) 0.19176(3) 0.04751(16) Uani d . 1 . . Br O9 0.1244(2) 0.31147(18) -0.02325(18) 0.0481(6) Uani d . 1 . . O O10 0.0460(2) 0.4206(2) 0.07845(18) 0.0481(7) Uani d . 1 . . O N8 0.1249(3) 0.3968(2) 0.0217(2) 0.0362(7) Uani d . 1 . . N N7 0.2165(2) 0.4743(2) 0.0047(2) 0.0365(7) Uani d . 1 . . N C4 0.3081(3) 0.4538(2) -0.0616(2) 0.0312(7) Uani d . 1 . . C C3 0.3291(3) 0.5347(3) -0.1255(2) 0.0386(8) Uani d . 1 . . C H3A 0.284(3) 0.602(3) -0.125(3) 0.053(11) Uiso d . 1 . . H C2 0.4147(3) 0.5157(3) -0.1910(3) 0.0385(8) Uani d . 1 . . C H2A 0.430(3) 0.570(3) -0.240(3) 0.049(11) Uiso d . 1 . . H N1 0.4808(3) 0.4194(2) -0.19363(19) 0.0347(7) Uani d . 1 . . N C6 0.4638(4) 0.3408(3) -0.1311(3) 0.0418(9) Uani d . 1 . . C H6A 0.513(3) 0.273(3) -0.143(2) 0.046(10) Uiso d . 1 . . H C5 0.3798(3) 0.3563(3) -0.0637(3) 0.0411(8) Uani d . 1 . . C H5A 0.370(4) 0.304(3) -0.016(3) 0.063(12) Uiso d . 1 . . H C12 0.5694(4) 0.3985(4) -0.2681(3) 0.0483(10) Uani d . 1 . . C H12A 0.593(5) 0.474(5) -0.296(3) 0.112(19) Uiso d . 1 . . H H12B 0.634(4) 0.347(4) -0.255(3) 0.071(13) Uiso d . 1 . . H H12C 0.532(5) 0.368(4) -0.313(3) 0.087(18) Uiso d . 1 . . H C11 0.2140(4) 0.5753(3) 0.0586(3) 0.0448(10) Uani d . 1 . . C H11A 0.226(4) 0.555(4) 0.120(4) 0.087(17) Uiso d . 1 . . H H11B 0.285(3) 0.620(3) 0.045(3) 0.050(11) Uiso d . 1 . . H H11C 0.132(4) 0.615(3) 0.052(3) 0.073(13) 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 Br 0.0521(2) 0.0396(2) 0.0508(3) -0.00500(17) 0.00366(19) -0.00610(17) O9 0.0562(15) 0.0379(14) 0.0502(17) -0.0126(12) 0.0006(13) -0.0071(13) O10 0.0435(14) 0.0508(15) 0.0501(17) 0.0014(11) 0.0099(13) 0.0064(13) N8 0.0377(14) 0.0334(15) 0.0375(18) -0.0034(13) -0.0042(14) 0.0090(14) N7 0.0399(15) 0.0315(14) 0.0381(18) -0.0055(12) 0.0042(13) -0.0006(13) C4 0.0340(16) 0.0281(15) 0.0316(19) -0.0055(14) -0.0033(14) 0.0011(14) C3 0.040(2) 0.0296(17) 0.046(2) 0.0044(16) -0.0001(17) 0.0068(16) C2 0.0394(18) 0.0322(16) 0.044(2) -0.0004(15) 0.0005(18) 0.0096(18) N1 0.0317(15) 0.0349(14) 0.0377(17) -0.0037(11) -0.0019(13) 0.0051(13) C6 0.049(2) 0.0295(17) 0.047(2) 0.0050(16) -0.0045(18) 0.0029(17) C5 0.050(2) 0.0312(18) 0.042(2) 0.0011(15) 0.0014(19) 0.0069(18) C12 0.045(2) 0.054(2) 0.046(3) 0.002(2) 0.005(2) -0.003(2) C11 0.048(2) 0.0352(19) 0.051(3) -0.0060(17) 0.0028(19) -0.0082(19) 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' Br Br -0.2901 2.4595 '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 O10 N8 O9 125.2(3) y O10 N8 N7 116.8(3) y O9 N8 N7 117.9(3) y N8 N7 C4 119.8(3) y N8 N7 C11 116.7(3) y C4 N7 C11 123.5(3) y C3 C4 C5 119.0(3) ? C3 C4 N7 118.7(3) ? C5 C4 N7 122.2(3) ? C2 C3 C4 119.7(3) ? N1 C2 C3 120.5(3) ? C6 N1 C2 120.8(3) ? C6 N1 C12 119.7(3) ? C2 N1 C12 119.5(3) ? N1 C6 C5 120.9(3) ? C6 C5 C4 119.0(3) ? 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 O9 N8 . 1.222(3) y O10 N8 . 1.221(4) y N8 N7 . 1.358(4) y N7 C4 . 1.403(4) y N7 C11 . 1.453(4) y C4 C3 . 1.379(4) ? C4 C5 . 1.387(4) ? C3 C2 . 1.350(5) ? C2 N1 . 1.343(4) ? N1 C6 . 1.339(4) ? N1 C12 . 1.474(5) y C6 C5 . 1.354(5) ? 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 O10 N8 N7 C4 -178.1(3) ? O9 N8 N7 C4 -1.2(4) ? O10 N8 N7 C11 2.5(5) ? O9 N8 N7 C11 179.4(3) ? N8 N7 C4 C3 129.3(3) y C11 N7 C4 C3 -51.3(5) ? N8 N7 C4 C5 -52.2(4) y C11 N7 C4 C5 127.2(4) ? C5 C4 C3 C2 2.9(5) ? N7 C4 C3 C2 -178.5(3) ? C4 C3 C2 N1 -1.0(5) ? C3 C2 N1 C6 -0.4(5) ? C3 C2 N1 C12 177.3(4) ? C2 N1 C6 C5 -0.1(5) ? C12 N1 C6 C5 -177.8(4) ? N1 C6 C5 C4 2.0(6) ? C3 C4 C5 C6 -3.3(5) ? N7 C4 C5 C6 178.1(3) ?