#------------------------------------------------------------------------------ #$Date: 2016-02-19 22:18:51 +0000 (Fri, 19 Feb 2016) $ #$Revision: 176760 $ #$URL: svn://www.crystallography.net/cod/cif/2/01/30/2013033.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_2013033 loop_ _publ_author_name 'Meszko, Joanna' 'Sikorski, Artur' 'Huta, Olexyj M.' 'Konitz, Antoni' 'B\/la\.zejowski, Jerzy' _publ_section_title ; 10-Methyl- and 9,10-dimethylacridinium methyl sulfate ; _journal_issue 11 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first o669 _journal_page_last o671 _journal_paper_doi 10.1107/S0108270102017171 _journal_volume 58 _journal_year 2002 _chemical_formula_moiety 'C15 H14 N + , C H3 O4 S -' _chemical_formula_sum 'C16 H17 N O4 S' _chemical_formula_weight 319.37 _chemical_name_systematic ; 9,10-dimethylacridinium methyl sulfate ; _space_group_IT_number 11 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yb' _symmetry_space_group_name_H-M 'P 1 21/m 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 90 _cell_angle_beta 96.24(3) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 9.271(2) _cell_length_b 6.8220(10) _cell_length_c 11.591(2) _cell_measurement_reflns_used 50 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 24 _cell_measurement_theta_min 6 _cell_volume 728.7(2) _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 1.00 _diffrn_measured_fraction_theta_max 1.00 _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 CuK\a _diffrn_radiation_wavelength 1.54178 _diffrn_reflns_av_R_equivalents 0.024 _diffrn_reflns_av_sigmaI/netI 0.011 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 1620 _diffrn_reflns_theta_full 71.99 _diffrn_reflns_theta_max 71.99 _diffrn_reflns_theta_min 3.84 _diffrn_standards_decay_% none _diffrn_standards_interval_count 200 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 2.143 _exptl_absorpt_correction_type none _exptl_crystal_colour red _exptl_crystal_density_diffrn 1.455 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 336 _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.35 _refine_diff_density_max 0.35 _refine_diff_density_min -0.28 _refine_ls_extinction_coef 0.070(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL97 (Sheldrick, 1997)' _refine_ls_goodness_of_fit_ref 1.128 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 131 _refine_ls_number_reflns 1565 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.128 _refine_ls_R_factor_all 0.048 _refine_ls_R_factor_gt 0.046 _refine_ls_shift/su_max <0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0839P)^2^+0.1827P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.135 _refine_ls_wR_factor_ref 0.137 _reflns_number_gt 1454 _reflns_number_total 1565 _reflns_threshold_expression I>2\s(I) _cod_data_source_file gg1138.cif _cod_data_source_block II _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_sg_symbol_H-M 'P 21/m' _cod_database_code 2013033 _cod_database_fobs_code 2013033 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' '-x, -y, -z' 'x, -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 S1 -0.02870(6) 0.2500 0.22575(5) 0.0485(3) Uani d S 1 . . S O1 0.1206(2) 0.2500 0.17339(18) 0.0771(8) Uani d S 1 . . O O2 0.0158(2) 0.2500 0.34805(17) 0.0721(7) Uani d S 1 . . O O3 -0.1032(2) 0.4224(3) 0.18400(14) 0.0893(6) Uani d . 1 . . O C1 0.3754(3) 0.2500 0.4159(2) 0.0460(6) Uani d S 1 . . C H1A 0.2746 0.2500 0.4116 0.055 Uiso d SR 1 . . H C2 0.4405(3) 0.2500 0.3169(2) 0.0528(6) Uani d S 1 . . C H2A 0.3842 0.2500 0.2454 0.063 Uiso d SR 1 . . H C3 0.5922(3) 0.2500 0.3213(2) 0.0561(7) Uani d S 1 . . C H3A 0.6357 0.2500 0.2526 0.067 Uiso d SR 1 . . H C4 0.6762(3) 0.2500 0.4246(2) 0.0502(6) Uani d S 1 . . C H4A 0.7767 0.2500 0.4259 0.060 Uiso d SR 1 . . H C5 0.4203(4) 0.2500 0.8427(3) 0.0689(9) Uani d S 1 . . C H5A 0.3201 0.2500 0.8430 0.083 Uiso d SR 1 . . H C6 0.5064(5) 0.2500 0.9443(3) 0.0868(12) Uani d S 1 . . C H6A 0.4648 0.2500 1.0137 0.104 Uiso d SR 1 . . H C7 0.6571(5) 0.2500 0.9464(3) 0.0900(13) Uani d S 1 . . C H7A 0.7147 0.2500 1.0173 0.108 Uiso d SR 1 . . H C8 0.7207(4) 0.2500 0.8463(3) 0.0695(9) Uani d S 1 . . C H8A 0.8214 0.2500 0.8493 0.083 Uiso d SR 1 . . H C9 0.3929(2) 0.2500 0.6296(2) 0.0389(5) Uani d S 1 . . C N10 0.6974(2) 0.2500 0.6354(2) 0.0471(5) Uani d S 1 . . N C11 0.4584(2) 0.2500 0.5263(2) 0.0391(5) Uani d S 1 . . C C12 0.6132(2) 0.2500 0.5307(2) 0.0402(5) Uani d S 1 . . C C13 0.4807(3) 0.2500 0.7354(2) 0.0469(6) Uani d S 1 . . C C14 0.6353(3) 0.2500 0.7379(2) 0.0474(6) Uani d S 1 . . C C15 0.2306(3) 0.2500 0.6277(2) 0.0535(7) Uani d S 1 . . C H15A 0.2030 0.1636 0.6868 0.080 Uiso d PR 0.50 . . H H15B 0.1977 0.3804 0.6417 0.080 Uiso d PR 0.50 . . H H15C 0.1874 0.2060 0.5531 0.080 Uiso d PR 0.50 . . H C16 0.8588(3) 0.2500 0.6377(3) 0.0658(8) Uani d S 1 . . C H16A 0.8858 0.3203 0.5716 0.099 Uiso d PR 0.50 . . H H16B 0.9012 0.3123 0.7075 0.099 Uiso d PR 0.50 . . H H16C 0.8930 0.1174 0.6355 0.099 Uiso d PR 0.50 . . H C17 0.1151(4) 0.2500 0.0489(3) 0.0790(11) Uani d S 1 . . C H17A 0.0293 0.1829 0.0162 0.118 Uiso d PR 0.50 . . H H17B 0.1993 0.1845 0.0263 0.118 Uiso d PR 0.50 . . H H17C 0.1133 0.3827 0.0212 0.118 Uiso d PR 0.50 . . 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 S1 0.0356(4) 0.0726(5) 0.0375(4) 0.000 0.0052(2) 0.000 O1 0.0404(10) 0.144(2) 0.0476(11) 0.000 0.0105(8) 0.000 O2 0.0527(11) 0.125(2) 0.0385(10) 0.000 0.0040(8) 0.000 O3 0.1036(13) 0.1001(14) 0.0641(9) 0.0445(12) 0.0082(9) 0.0005(9) C1 0.0364(11) 0.0523(13) 0.0487(13) 0.000 0.0012(10) 0.000 C2 0.0519(14) 0.0625(16) 0.0430(13) 0.000 0.0014(11) 0.000 C3 0.0530(14) 0.0677(17) 0.0502(14) 0.000 0.0175(11) 0.000 C4 0.0366(12) 0.0576(15) 0.0589(15) 0.000 0.0160(11) 0.000 C5 0.0612(17) 0.100(3) 0.0469(15) 0.000 0.0130(13) 0.000 C6 0.083(2) 0.132(4) 0.0453(16) 0.000 0.0083(15) 0.000 C7 0.084(2) 0.134(4) 0.0472(17) 0.000 -0.0138(16) 0.000 C8 0.0528(16) 0.095(2) 0.0573(17) 0.000 -0.0101(13) 0.000 C9 0.0323(11) 0.0421(11) 0.0428(12) 0.000 0.0067(9) 0.000 N10 0.0336(10) 0.0504(11) 0.0566(13) 0.000 0.0015(8) 0.000 C11 0.0313(11) 0.0410(11) 0.0452(12) 0.000 0.0053(9) 0.000 C12 0.0322(11) 0.0400(11) 0.0484(13) 0.000 0.0047(9) 0.000 C13 0.0422(13) 0.0535(14) 0.0451(13) 0.000 0.0052(10) 0.000 C14 0.0422(13) 0.0506(13) 0.0482(13) 0.000 -0.0007(10) 0.000 C15 0.0340(12) 0.0710(17) 0.0567(15) 0.000 0.0107(10) 0.000 C16 0.0319(12) 0.092(2) 0.0716(19) 0.000 -0.0024(12) 0.000 C17 0.0658(19) 0.124(3) 0.0503(16) 0.000 0.0219(14) 0.000 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 '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 O1 S1 O2 102.19(11) yes O1 S1 O3 106.54(10) ? O2 S1 O3 114.44(8) yes C17 O1 S1 116.82(19) yes C2 C1 C11 121.0(2) ? C2 C1 H1A 119.5 ? C11 C1 H1A 119.5 ? C1 C2 C3 120.5(2) ? C1 C2 H2A 119.8 ? C3 C2 H2A 119.8 ? C4 C3 C2 120.6(3) ? C4 C3 H3A 119.7 ? C2 C3 H3A 119.7 ? C3 C4 C12 121.0(2) ? C3 C4 H4A 119.5 ? C12 C4 H4A 119.5 ? C6 C5 C13 120.9(3) ? C6 C5 H5A 119.6 ? C13 C5 H5A 119.6 ? C5 C6 C7 120.8(3) ? C5 C6 H6A 119.6 ? C7 C6 H6A 119.6 ? C8 C7 C6 120.8(3) ? C8 C7 H7A 119.6 ? C6 C7 H7A 119.6 ? C7 C8 C14 120.5(3) ? C7 C8 H8A 119.8 ? C14 C8 H8A 119.8 ? C13 C9 C11 119.0(2) ? C13 C9 C15 120.0(2) ? C11 C9 C15 120.9(2) yes C12 N10 C14 120.8(2) ? C12 N10 C16 119.3(2) yes C14 N10 C16 119.8(2) ? C9 C11 C1 121.8(2) ? C9 C11 C12 119.7(2) ? C1 C11 C12 118.5(2) ? N10 C12 C4 121.3(2) ? N10 C12 C11 120.4(2) ? C4 C12 C11 118.4(2) ? C9 C13 C5 121.5(3) ? C9 C13 C14 120.3(2) ? C5 C13 C14 118.2(3) ? N10 C14 C8 121.4(2) ? N10 C14 C13 119.7(2) ? C8 C14 C13 118.8(3) ? C9 C15 H15A 109.5 ? C9 C15 H15B 109.5 ? H15A C15 H15B 109.5 ? C9 C15 H15C 109.5 ? H15A C15 H15C 109.5 ? H15B C15 H15C 109.5 ? N10 C16 H16A 109.5 ? N10 C16 H16B 109.5 ? H16A C16 H16B 109.5 ? N10 C16 H16C 109.5 ? H16A C16 H16C 109.5 ? H16B C16 H16C 109.5 ? O1 C17 H17A 109.5 ? O1 C17 H17B 109.5 ? H17A C17 H17B 109.5 ? O1 C17 H17C 109.5 ? H17A C17 H17C 109.5 ? H17B C17 H17C 109.5 ? 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 S1 O1 . 1.571(2) yes S1 O2 . 1.433(2) yes S1 O3 . 1.4221(18) yes O1 C17 . 1.438(4) yes C1 C2 . 1.354(4) ? C1 C11 . 1.419(3) ? C1 H1A . 0.9300 ? C2 C3 . 1.402(4) ? C2 H2A . 0.9300 ? C3 C4 . 1.356(4) ? C3 H3A . 0.9300 ? C4 C12 . 1.417(4) ? C4 H4A . 0.9300 ? C5 C6 . 1.349(5) ? C5 C13 . 1.418(4) ? C5 H5A . 0.9300 ? C6 C7 . 1.395(6) ? C6 H6A . 0.9300 ? C7 C8 . 1.357(5) ? C7 H7A . 0.9300 ? C8 C14 . 1.412(4) ? C8 H8A . 0.9300 ? C9 C13 . 1.396(3) ? C9 C11 . 1.401(3) ? C9 C15 . 1.502(3) yes N10 C12 . 1.370(3) ? N10 C14 . 1.376(4) ? N10 C16 . 1.493(3) yes C11 C12 . 1.430(3) ? C13 C14 . 1.430(3) ? C15 H15A . 0.9600 ? C15 H15B . 0.9600 ? C15 H15C . 0.9600 ? C16 H16A . 0.9600 ? C16 H16B . 0.9600 ? C16 H16C . 0.9600 ? C17 H17A . 0.9600 ? C17 H17B . 0.9600 ? C17 H17C . 0.9600 ? 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 C1 H1A O2 1_555 1_555 1_555 0.93 2.43 3.341(3) 166 yes C2 H2A O1 1_555 1_555 1_555 0.93 2.49 3.239(4) 137 yes C4 H4A O2 1_555 1_555 1_655 0.93 2.48 3.363(4) 158 yes C15 H15A O3 1_555 1_555 2_546 0.96 2.47 3.423(3) 171 yes C15 H15A O3 1_555 4_555 3_566 0.96 2.47 3.423(3) 171 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 _geom_torsion_publ_flag O3 S1 O1 C17 -59.62(8) ? O2 S1 O1 C17 180.0 yes C11 C1 C2 C3 0.0 ? C1 C2 C3 C4 0.0 ? C2 C3 C4 C12 0.0 ? C13 C5 C6 C7 0.0 ? C5 C6 C7 C8 0.0 ? C6 C7 C8 C14 0.0 ? C13 C9 C11 C1 180.0 ? C15 C9 C11 C1 0.0 ? C13 C9 C11 C12 0.0 ? C15 C9 C11 C12 180.0 yes C2 C1 C11 C9 180.0 ? C2 C1 C11 C12 0.0 ? C14 N10 C12 C4 180.0 ? C16 N10 C12 C4 0.0 ? C14 N10 C12 C11 0.0 ? C16 N10 C12 C11 180.0 ? C3 C4 C12 N10 180.0 ? C3 C4 C12 C11 0.0 ? C9 C11 C12 N10 0.0 ? C1 C11 C12 N10 180.0 ? C9 C11 C12 C4 180.0 ? C1 C11 C12 C4 0.0 ? C11 C9 C13 C5 180.0 ? C15 C9 C13 C5 0.0 ? C11 C9 C13 C14 0.0 yes C15 C9 C13 C14 180.0 ? C6 C5 C13 C9 180.0 ? C6 C5 C13 C14 0.0 ? C12 N10 C14 C8 180.0 ? C16 N10 C14 C8 0.0 ? C12 N10 C14 C13 0.0 yes C16 N10 C14 C13 180.0 ? C7 C8 C14 N10 180.0 ? C7 C8 C14 C13 0.0 ? C9 C13 C14 N10 0.0 ? C5 C13 C14 N10 180.0 ? C9 C13 C14 C8 180.0 ? C5 C13 C14 C8 0.0 ? S1 O1 C17 H17A -30.4 yes C11 C9 C15 H15A 139.4 yes C12 N10 C16 H16A 32.0 yes