#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 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'
'Błażejowski, 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       θ/2θ
_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+0.001xFc²λ³/sin(2θ)]^-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/[σ²(Fo²)+(0.0839P)²+0.1827P] where P=(Fo²+2Fc²)/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>2σ(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_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
