#------------------------------------------------------------------------------ #$Date: 2016-02-19 22:18:51 +0000 (Fri, 19 Feb 2016) $ #$Revision: 176760 $ #$URL: svn://www.crystallography.net/cod/cif/2/01/26/2012682.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_2012682 loop_ _publ_author_name 'Huta, Olexyj M.' 'Patsaj, Ihor O.' 'Konitz, Antoni' 'Meszko, Joanna' 'B\/la\.zejowski, Jerzy' _publ_section_title ; 9-Cyano-10-methylacridinium hydrogen dinitrate ; _journal_issue 5 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first o295 _journal_page_last o297 _journal_paper_doi 10.1107/S0108270102004912 _journal_volume 58 _journal_year 2002 _chemical_formula_moiety 'C15 H11 N2 + , H N2 O6 -' _chemical_formula_sum 'C15 H12 N4 O6' _chemical_formula_weight 344.29 _chemical_name_systematic ; 9-Cyano-10-methylacridinium hydrogen dinitrate ; _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 _cell_angle_alpha 90 _cell_angle_beta 115.96(4) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 12.799(4) _cell_length_b 10.015(3) _cell_length_c 13.168(4) _cell_measurement_reflns_used 50 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 24.0 _cell_measurement_theta_min 6.0 _cell_volume 1517.6(10) _computing_cell_refinement 'KM-4 Software' _computing_data_collection 'KM-4 Software (Kuma Diffraction, 1989)' _computing_data_reduction 'KM-4 Software' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full 0.965 _diffrn_measured_fraction_theta_max 0.965 _diffrn_measurement_device_type 'Kuma KM-4' _diffrn_measurement_method \q/2\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 0.000 _diffrn_reflns_av_sigmaI/netI 0.023 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 2003 _diffrn_reflns_theta_full 28.99 _diffrn_reflns_theta_max 28.99 _diffrn_reflns_theta_min 2.70 _diffrn_standards_decay_% 3.6 _diffrn_standards_interval_count 200 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.120 _exptl_absorpt_correction_type none _exptl_crystal_colour green _exptl_crystal_density_diffrn 1.507 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 712 _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.15 _refine_diff_density_max 0.25 _refine_diff_density_min -0.26 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.066 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 125 _refine_ls_number_reflns 2003 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.066 _refine_ls_R_factor_all 0.101 _refine_ls_R_factor_gt 0.047 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.096P)^2^+0.220P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.141 _refine_ls_wR_factor_ref 0.169 _reflns_number_gt 1104 _reflns_number_total 2003 _reflns_threshold_expression I>2\s(I) _cod_data_source_file bm1487.cif _cod_data_source_block I _cod_depositor_comments ; 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 1517.6(8) _cod_original_sg_symbol_H-M 'C 2/c' _cod_database_code 2012682 _cod_database_fobs_code 2012682 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_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 0.11298(16) 0.6781(2) 0.45717(15) 0.0516(5) Uani d . 1 . . C H1A 0.10942 0.7739 0.45747 0.063(6) Uiso d R 1 . . H C2 0.16584(18) 0.6095(2) 0.55404(17) 0.0616(6) Uani d . 1 . . C H2A 0.20713 0.6572 0.62351 0.086(8) Uiso d R 1 . . H C3 0.16546(19) 0.4700(2) 0.55297(18) 0.0650(6) Uani d . 1 . . C H3A 0.20272 0.4182 0.62079 0.093(8) Uiso d R 1 . . H C4 0.11164(18) 0.3993(2) 0.45533(18) 0.0580(5) Uani d . 1 . . C H4A 0.11071 0.3035 0.45351 0.074(7) Uiso d R 1 . . H C9 0.0000 0.6776(2) 0.2500 0.0407(5) Uani d S 1 . . C N10 0.0000 0.40130(18) 0.2500 0.0450(5) Uani d S 1 . . N C11 0.05554(14) 0.60999(16) 0.35227(14) 0.0411(4) Uani d . 1 . . C C12 0.05463(15) 0.46744(16) 0.35101(15) 0.0437(4) Uani d . 1 . . C C15 0.0000 0.8218(2) 0.2500 0.0516(6) Uani d S 1 . . C N2 0.0000 0.9351(2) 0.2500 0.0780(9) Uani d S 1 . . N C16 0.0000 0.2535(3) 0.2500 0.0694(9) Uani d S 1 . . C H16A -0.0052 0.2216(3) 0.1792 0.104 Uiso d PR 0.50 . . H H16B -0.0654 0.2216(3) 0.2604 0.104 Uiso d PR 0.50 . . H H16C 0.0705 0.2216(3) 0.3104 0.104 Uiso d PR 0.50 . . H N1 0.16168(15) -0.06181(17) 0.11855(14) 0.0541(4) Uani d . 1 . . N O1 0.06814(13) -0.09328(15) 0.02957(13) 0.0674(5) Uani d . 1 . . O O2 0.22574(15) -0.15292(19) 0.16909(13) 0.0796(5) Uani d . 1 . . O O3 0.18071(17) 0.05459(17) 0.14531(16) 0.0817(6) Uani d . 1 . . O H1B 0.000(4) 0.000(7) 0.000(6) 0.105(13) Uiso d S 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 0.0509(10) 0.0533(11) 0.0519(10) -0.0047(8) 0.0238(8) -0.0059(8) C2 0.0564(12) 0.0773(15) 0.0483(11) -0.0046(10) 0.0203(9) -0.0022(9) C3 0.0552(12) 0.0822(16) 0.0526(12) 0.0059(11) 0.0189(10) 0.0191(10) C4 0.0572(12) 0.0482(11) 0.0680(13) 0.0049(9) 0.0269(11) 0.0161(9) C9 0.0434(12) 0.0329(11) 0.0509(13) 0.000 0.0253(11) 0.000 N10 0.0443(11) 0.0284(9) 0.0606(13) 0.000 0.0213(10) 0.000 C11 0.0405(8) 0.0372(8) 0.0482(9) -0.0020(7) 0.0219(7) -0.0011(6) C12 0.0396(8) 0.0380(8) 0.0539(10) 0.0001(7) 0.0207(8) 0.0047(7) C15 0.0669(17) 0.0399(13) 0.0543(14) 0.000 0.0323(13) 0.000 N2 0.121(3) 0.0404(14) 0.091(2) 0.000 0.063(2) 0.000 C16 0.0731(19) 0.0284(11) 0.091(2) 0.000 0.0216(17) 0.000 N1 0.0527(9) 0.0604(11) 0.0475(9) 0.0005(8) 0.0203(8) 0.0026(8) O1 0.0599(9) 0.0544(8) 0.0662(9) 0.0058(7) 0.0075(7) -0.0108(7) O2 0.0743(10) 0.0881(12) 0.0672(10) 0.0266(9) 0.0224(8) 0.0163(9) O3 0.0793(12) 0.0695(11) 0.0798(12) -0.0193(9) 0.0195(9) -0.0137(8) 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 C11 C9 C15 119.08(10) yes C12 N10 C16 118.87(10) yes O1 N1 O2 116.65(17) yes O1 N1 O3 119.07(17) yes O2 N1 O3 124.27(19) yes N1 O1 H1B 110.55(13) yes H1A C1 C2 120.85 no H1A C1 C11 118.53 no C2 C1 C11 120.53(19) no H2A C2 C1 119.26 no H2A C2 C3 120.37 no C1 C2 C3 120.30(19) no H3A C3 C4 115.96 no H3A C3 C2 122.20 no C4 C3 C2 121.84(19) no H4A C4 C3 122.62 no H4A C4 C12 117.50 no C3 C4 C12 119.88(19) no C9 C11 C1 122.26(16) no C9 C11 C12 118.47(15) no C1 C11 C12 119.27(15) no N10 C12 C4 122.35(17) no N10 C12 C11 119.48(15) no C4 C12 C11 118.18(16) no H16C C16 H16A 109.5 no H16C C16 H16B 109.5 no H16A C16 H16B 109.5 no H16C C16 N10 109.5 no H16A C16 N10 109.5 no H16B C16 N10 109.5 no 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 C9 C15 . 1.444(3) yes N10 C16 . 1.480(3) yes C15 N2 . 1.135(3) yes N1 O1 . 1.295(2) yes N1 O2 . 1.212(2) yes N1 O3 . 1.211(2) yes O1 H1B . 1.220(2) yes C1 H1A . 0.9599 no C1 C2 . 1.343(3) no C1 C11 . 1.423(2) no C2 H2A . 0.9598 no C2 C3 . 1.397(3) no C3 H3A . 0.9598 no C3 C4 . 1.361(3) no C4 H4A . 0.9601 no C4 C12 . 1.417(3) no C9 C11 . 1.392(2) no N10 C12 . 1.372(2) no C11 C12 . 1.428(2) no C16 H16C . 0.9600 no C16 H16A . 0.9600 no C16 H16B . 0.9600 no loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_D _geom_hbond_site_symmetry_H _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 C2 H2A O2 7_556 7_556 1_555 0.96 2.48 3.313(3) 145 yes C4 H4A O1 1_555 1_555 6_556 0.96 2.49 3.337(3) 147 yes O1 H1B O1 1_555 1_555 5_555 1.22 1.22 2.440(4) 180 yes 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_site_symmetry_1 _geom_torsion _geom_torsion_publ_flag C11 C9 C11 C12 2 -0.13(11) yes C12 N10 C12 C11 2 -0.13(11) yes C11 C1 C2 C3 . 0.2(3) no C1 C2 C3 C4 . -0.5(3) no C2 C3 C4 C12 . 0.4(3) no C15 C9 C11 C1 . -0.29(18) no C15 C9 C11 C12 . 179.87(11) no C2 C1 C11 C9 . -179.83(16) no C2 C1 C11 C12 . 0.0(3) no C16 N10 C12 C4 . 0.36(19) no C16 N10 C12 C11 . 179.87(11) no C3 C4 C12 N10 . 179.35(17) no C3 C4 C12 C11 . -0.2(3) no C9 C11 C12 N10 . 0.3(2) no C1 C11 C12 N10 . -179.58(14) no C9 C11 C12 C4 . 179.79(14) no C1 C11 C12 C4 . -0.1(2) no