#------------------------------------------------------------------------------
#$Date: 2017-10-13 02:48:21 +0200 (vie 13 de oct de 2017) $
#$Revision: 201957 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/88/2018830.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_2018830
loop_
_publ_author_name
'Chernyshev, Vladimir V.'
'Petkune, Sanita'
'Actins, Andris'
'Auzins, Raimonds'
'Davlyatshin, Dmitry I.'
'Nosyrev, Pavel V.'
'Velikodny, Yurii A.'
_publ_section_title
;
 Two polymorphs of afobazole from powder diffraction data
;
_journal_coeditor_code           SF3190
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              299
_journal_page_last               302
_journal_paper_doi               10.1107/S0108270113004502
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          'C15 H23 N3 O2 S 2+ , 2Cl -'
_chemical_formula_moiety         'C15 H23 N3 O2 S 2+, 2 (Cl -)'
_chemical_formula_sum            'C15 H23 Cl2 N3 O2 S'
_chemical_formula_weight         380.33
_chemical_melting_point          473
_chemical_name_common            afobazole
_chemical_name_systematic
;
5-Ethoxy-2-[2-(morpholin-4-ium-4-yl)ethylsulfanyl]-1H-benzimidazol-3-ium
dichloride
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.858(15)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.4952(15)
_cell_length_b                   16.5419(19)
_cell_length_c                   7.9715(8)
_cell_measurement_reflns_used    1062
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      38.494
_cell_measurement_theta_min      3.049
_cell_volume                     1911.2(4)
_computing_cell_refinement       'MRIA (Zlokazov & Chernyshev, 1992)'
_computing_data_collection
'G670 Imaging-Plate Guinier Camera Software (Huber, 2002)'
_computing_data_reduction
'G670 Imaging-Plate Guinier Camera Software (Huber, 2002)'
_computing_molecular_graphics
;
PLATON (Spek, 2009) and Mercury (Macrae et al., 2008)
;
_computing_publication_material
;
MRIA (Zlokazov & Chernyshev, 1992) and SHELXL97 (Sheldrick,
2008)
;
_computing_structure_refinement  'MRIA (Zlokazov & Chernyshev, 1992)'
_computing_structure_solution
'simulated annealing (Zhukov et al., 2001)'
_diffrn_ambient_temperature      298(2)
_diffrn_measurement_device_type  'Huber G670 Guinier camera'
_diffrn_radiation_monochromator  'curved germanium(111)'
_diffrn_radiation_source         'line-focus sealed tube'
_diffrn_radiation_type           CuK\a~1~
_diffrn_radiation_wavelength     1.54059
_exptl_absorpt_coefficient_mu    4.173
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             800
_pd_block_diffractogram_id       Form_II_pattern
_pd_char_colour                  white
_pd_char_particle_morphology     'no specific habit'
_pd_instr_location
;
Department of Chemistry, Moscow State University, 119991 Moscow, Russia
;
_pd_meas_2theta_range_inc        0.01
_pd_meas_2theta_range_max        76.00
_pd_meas_2theta_range_min        4.00
_pd_meas_number_of_points        7201
_pd_meas_scan_method             cont
_pd_prep_pressure                101
_pd_prep_temperature             298(2)
_pd_proc_2theta_range_inc        0.01
_pd_proc_2theta_range_max        76.00
_pd_proc_2theta_range_min        4.00
_pd_proc_info_excluded_regions   none
_pd_proc_ls_background_function  'Chebyshev polynomial up to the 5th order'
_pd_proc_ls_pref_orient_corr     none
_pd_proc_ls_profile_function     'split-type pseudo-Voigt (Toraya, 1986)'
_pd_proc_ls_prof_R_factor        0.0192
_pd_proc_ls_prof_wR_expected     0.0132
_pd_proc_ls_prof_wR_factor       0.0223
_pd_proc_wavelength              1.54059
_pd_spec_mounting
;
thin layer in the specimen holder of the camera
;
_pd_spec_mount_mode              transmission
_pd_spec_shape                   'flat sheet'
_pd_spec_size_axial              15
_pd_spec_size_equat              1
_pd_spec_size_thick              1
_refine_diff_density_max         0.38
_refine_diff_density_min         -0.35
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.6942
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           fullcycle
_refine_ls_number_constraints    0
_refine_ls_number_parameters     127
_refine_ls_number_restraints     68
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Inet
_refine_ls_weighting_scheme      sigma
_cod_data_source_file            sf3190.cif
_cod_data_source_block           II
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2018830
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, -y+1/2, z+1/2'
'-x, -y, -z'
'-x, y-1/2, -z-1/2'
loop_
_atom_site_type_symbol
_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_occupancy
_atom_site_symmetry_multiplicity
N N1 0.7461(7) 0.6121(7) 0.4652(14) 0.063(5) Uiso d 1 1
H H1 0.7658 0.5638 0.4481 0.076 Uiso calc 1 1
C C2 0.6643(10) 0.6304(8) 0.5351(17) 0.061(7) Uiso d 1 1
N N3 0.6580(8) 0.7131(7) 0.5384(14) 0.059(5) Uiso d 1 1
H H3 0.6126 0.7400 0.5788 0.071 Uiso calc 1 1
C C4 0.7628(10) 0.8279(10) 0.4499(18) 0.070(7) Uiso d 1 1
H H4 0.7268 0.8704 0.4880 0.084 Uiso calc 1 1
C C5 0.8488(11) 0.8408(8) 0.370(2) 0.067(6) Uiso d 1 1
C C6 0.9048(11) 0.7742(9) 0.3214(19) 0.067(7) Uiso d 1 1
H H6 0.9597 0.7846 0.2667 0.080 Uiso calc 1 1
C C7 0.8805(11) 0.6946(9) 0.3518(19) 0.070(6) Uiso d 1 1
H H7 0.9193 0.6519 0.3254 0.084 Uiso calc 1 1
C C8 0.7940(10) 0.6819(9) 0.4248(16) 0.057(6) Uiso d 1 1
C C9 0.7361(10) 0.7474(10) 0.467(2) 0.074(6) Uiso d 1 1
O O10 0.8822(6) 0.9136(5) 0.3406(11) 0.054(4) Uiso d 1 1
C C11 0.9669(10) 0.9267(9) 0.2491(18) 0.061(6) Uiso d 1 1
H H11A 0.9644 0.8987 0.1421 0.073 Uiso calc 1 1
H H11B 1.0196 0.9069 0.3132 0.073 Uiso calc 1 1
C C12 0.9743(11) 1.0180(9) 0.2224(17) 0.069(7) Uiso d 1 1
H H12A 1.0295 1.0299 0.1619 0.104 Uiso calc 1 1
H H12B 0.9766 1.0447 0.3292 0.104 Uiso calc 1 1
H H12C 0.9216 1.0367 0.1592 0.104 Uiso calc 1 1
S S13 0.5883(3) 0.5626(2) 0.6276(5) 0.053(2) Uiso d 1 1
C C14 0.4898(11) 0.6262(9) 0.6950(18) 0.066(6) Uiso d 1 1
H H14A 0.5112 0.6774 0.7406 0.079 Uiso calc 1 1
H H14B 0.4475 0.6366 0.6022 0.079 Uiso calc 1 1
C C15 0.4433(10) 0.5741(9) 0.8325(18) 0.069(7) Uiso d 1 1
H H15A 0.4379 0.5187 0.7941 0.083 Uiso calc 1 1
H H15B 0.4813 0.5745 0.9337 0.083 Uiso calc 1 1
N N16 0.3487(8) 0.6070(7) 0.8707(14) 0.059(5) Uiso d 1 1
H H16 0.3102 0.5922 0.7849 0.071 Uiso calc 1 1
C C17 0.3482(11) 0.6998(9) 0.879(2) 0.075(6) Uiso d 1 1
H H17A 0.3932 0.7181 0.9624 0.090 Uiso calc 1 1
H H17B 0.3649 0.7221 0.7715 0.090 Uiso calc 1 1
C C18 0.2532(10) 0.7292(9) 0.9263(19) 0.071(7) Uiso d 1 1
H H18A 0.2547 0.7875 0.9389 0.086 Uiso calc 1 1
H H18B 0.2101 0.7165 0.8358 0.086 Uiso calc 1 1
O O19 0.2213(6) 0.6943(6) 1.0765(10) 0.058(4) Uiso d 1 1
C C20 0.2146(10) 0.6087(10) 1.0605(17) 0.069(6) Uiso d 1 1
H H20A 0.1734 0.5953 0.9675 0.083 Uiso calc 1 1
H H20B 0.1891 0.5861 1.1620 0.083 Uiso calc 1 1
C C21 0.3101(10) 0.5720(8) 1.0300(18) 0.066(7) Uiso d 1 1
H H21A 0.3511 0.5841 1.1240 0.079 Uiso calc 1 1
H H21B 0.3051 0.5137 1.0199 0.079 Uiso calc 1 1
Cl Cl1 0.2325(3) 0.5693(2) 0.5691(5) 0.0539(18) Uiso d 1 1
Cl Cl2 0.5306(3) 0.8426(2) 0.6990(5) 0.0601(19) Uiso d 1 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Cl Cl 0.3639 0.7018 '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'
O O 0.0492 0.0322 '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'
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C2 N1 C8 110.8(12)
C2 N1 H1 124.6
C8 N1 H1 124.6
N1 C2 N3 106.9(12)
N1 C2 S13 126.5(11)
N3 C2 S13 126.2(11)
C2 N3 C9 110.0(12)
C2 N3 H3 124.9
C9 N3 H3 125.0
C9 C4 C5 115.7(14)
C9 C4 H4 122.1
C5 C4 H4 122.2
O10 C5 C4 122.9(13)
O10 C5 C6 116.3(13)
C4 C5 C6 120.8(13)
C7 C6 C5 122.6(14)
C7 C6 H6 118.7
C5 C6 H6 118.7
C6 C7 C8 116.5(14)
C6 C7 H7 121.8
C8 C7 H7 121.7
N1 C8 C7 132.3(13)
N1 C8 C9 106.4(12)
C7 C8 C9 121.3(14)
C4 C9 N3 131.0(14)
C4 C9 C8 122.8(14)
N3 C9 C8 105.9(13)
C5 O10 C11 122.7(11)
O10 C11 C12 106.2(11)
O10 C11 H11A 110.4
C12 C11 H11A 110.5
O10 C11 H11B 110.4
C12 C11 H11B 110.5
H11A C11 H11B 108.7
C11 C12 H12A 109.5
C11 C12 H12B 109.5
H12A C12 H12B 109.5
C11 C12 H12C 109.5
H12A C12 H12C 109.4
H12B C12 H12C 109.4
C2 S13 C14 104.5(7)
C15 C14 S13 103.5(10)
C15 C14 H14A 111.1
S13 C14 H14A 111.1
C15 C14 H14B 111.0
S13 C14 H14B 111.0
H14A C14 H14B 109.0
N16 C15 C14 110.3(12)
N16 C15 H15A 109.6
C14 C15 H15A 109.6
N16 C15 H15B 109.6
C14 C15 H15B 109.6
H15A C15 H15B 108.1
C21 N16 C15 112.4(11)
C21 N16 C17 110.1(11)
C15 N16 C17 111.9(11)
C21 N16 H16 107.4
C15 N16 H16 107.4
C17 N16 H16 107.4
C18 C17 N16 109.7(12)
C18 C17 H17A 109.7
N16 C17 H17A 109.7
C18 C17 H17B 109.8
N16 C17 H17B 109.7
H17A C17 H17B 108.3
O19 C18 C17 112.9(12)
O19 C18 H18A 109.0
C17 C18 H18A 109.0
O19 C18 H18B 109.1
C17 C18 H18B 109.1
H18A C18 H18B 107.7
C18 O19 C20 110.7(10)
O19 C20 C21 110.3(12)
O19 C20 H20A 109.6
C21 C20 H20A 109.6
O19 C20 H20B 109.6
C21 C20 H20B 109.6
H20A C20 H20B 108.1
N16 C21 C20 109.1(11)
N16 C21 H21A 109.8
C20 C21 H21A 109.9
N16 C21 H21B 109.8
C20 C21 H21B 109.9
H21A C21 H21B 108.3
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C2 1.352(18)
N1 C8 1.388(19)
N1 H1 0.86
C2 N3 1.372(18)
C2 S13 1.743(14)
N3 C9 1.396(19)
N3 H3 0.86
C4 C9 1.39(2)
C4 C5 1.42(2)
C4 H4 0.93
C5 O10 1.321(17)
C5 C6 1.43(2)
C6 C7 1.38(2)
C6 H6 0.93
C7 C8 1.41(2)
C7 H7 0.93
C8 C9 1.41(2)
O10 C11 1.438(17)
C11 C12 1.53(2)
C11 H11A 0.97
C11 H11B 0.97
C12 H12A 0.96
C12 H12B 0.96
C12 H12C 0.96
S13 C14 1.859(16)
C14 C15 1.56(2)
C14 H14A 0.97
C14 H14B 0.97
C15 N16 1.510(19)
C15 H15A 0.97
C15 H15B 0.97
N16 C21 1.510(18)
N16 C17 1.537(18)
N16 H16 0.91
C17 C18 1.51(2)
C17 H17A 0.97
C17 H17B 0.97
C18 O19 1.414(17)
C18 H18A 0.97
C18 H18B 0.97
O19 C20 1.424(19)
C20 C21 1.53(2)
C20 H20A 0.97
C20 H20B 0.97
C21 H21A 0.97
C21 H21B 0.97
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
N1 H1 Cl1 3_666 0.86 2.21 3.030(12) 160
N3 H3 Cl2 . 0.86 2.29 3.116(12) 161
N16 H16 Cl1 . 0.91 2.08 2.981(12) 172
C15 H15B Cl2 2_565 0.97 2.61 3.453(15) 145
C18 H18A Cl1 2_565 0.97 2.61 3.536(15) 160
C18 H18B O19 2_564 0.97 2.55 3.091(17) 115
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9524442
