#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/13/2011305.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_2011305
loop_
_publ_author_name
'Boryczka, Stanisław'
'Steiner, Thomas'
_publ_section_title
;
 Hydrogen bonding in two salts of
 3-methylthio-4-(propargylthio)quinoline
;
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1139
_journal_page_last               1141
_journal_paper_doi               10.1107/S0108270100008271
_journal_volume                  56
_journal_year                    2000
_chemical_formula_moiety         'C13 H12 N S2 + , C2 Cl3 O2 -'
_chemical_formula_sum            'C15 H12 Cl3 N O2 S2'
_chemical_formula_weight         408.73
_chemical_name_systematic
;
 4-Methylthio-3-propargylthioquinolinium trichloroacetate
;
_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'
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 111.67(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   19.430(11)
_cell_length_b                   5.338(3)
_cell_length_c                   36.66(3)
_cell_measurement_reflns_used    26
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      15.1
_cell_measurement_theta_min      5.0
_cell_volume                     3534(4)
_computing_cell_refinement       'please provide details'
_computing_data_collection       'please provide details'
_computing_data_reduction        'please provide details'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293
_diffrn_measured_fraction_theta_full .994
_diffrn_measured_fraction_theta_max .994
_diffrn_measurement_device_type  'STOE four-circle'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     .71073
_diffrn_reflns_av_R_equivalents  .032
_diffrn_reflns_av_sigmaI/netI    .042
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       2
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       47
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_number            4098
_diffrn_reflns_theta_full        27.54
_diffrn_reflns_theta_max         27.54
_diffrn_reflns_theta_min         2.13
_diffrn_standards_decay_%        6
_diffrn_standards_interval_time  90
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    .761
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.537
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1664
_exptl_crystal_size_max          1.2
_exptl_crystal_size_mid          .1
_exptl_crystal_size_min          .05
_refine_diff_density_max         .56
_refine_diff_density_min         -.43
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     224
_refine_ls_number_reflns         4031
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.011
_refine_ls_R_factor_all          .093
_refine_ls_R_factor_gt           .056
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         .000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0764P)²+5.2477P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         .165
_reflns_number_gt                2781
_reflns_number_total             4031
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            de1147.cif
_cod_data_source_block           III
_cod_original_cell_volume        3533(4)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2011305
_cod_database_fobs_code          2011305
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
S1 .14430(6) .3416(2) .03462(3) .0626(3) Uani d . 1 . . S
S2 .05253(5) -.00203(18) .07042(3) .0556(3) Uani d . 1 . . S
N1 .19773(15) .6183(5) .14213(8) .0412(6) Uani d . 1 . . N
H1 .230(2) .741(9) .1550(12) .066(13) Uiso d . 1 . . H
C2 .19199(18) .5839(7) .10568(10) .0440(8) Uani d . 1 . . C
H2 .2172 .6907 .0949 .053(11) Uiso calc R 1 . . H
C3 .14879(18) .3902(7) .08256(9) .0422(7) Uani d . 1 . . C
C4 .10912(16) .2401(6) .09870(9) .0393(7) Uani d . 1 . . C
C5 .11634(16) .2755(6) .13815(9) .0385(7) Uani d . 1 . . C
C6 .08055(19) .1282(7) .15765(11) .0487(8) Uani d . 1 . . C
H6 .0490 .0004 .1441 .041(9) Uiso calc R 1 . . H
C7 .0912(2) .1687(8) .19567(12) .0555(9) Uani d . 1 . . C
H7 .0672 .0673 .2079 .047(10) Uiso calc R 1 . . H
C8 .1381(2) .3624(8) .21719(11) .0560(10) Uani d . 1 . . C
H8 .1450 .3878 .2434 .044(9) Uiso calc R 1 . . H
C9 .1730(2) .5116(7) .19942(10) .0485(8) Uani d . 1 . . C
H9 .2036 .6407 .2134 .064(12) Uiso calc R 1 . . H
C10 .16300(17) .4708(6) .15992(9) .0391(7) Uani d . 1 . . C
C11 .2164(3) .5331(15) .03144(14) .093(2) Uani d . 1 . . C
H11A .2043 .7061 .0330 .12(3) Uiso calc R 1 . . H
H11B .2222 .5030 .0069 .085(15) Uiso calc R 1 . . H
H11C .2619 .4940 .0527 .089(17) Uiso calc R 1 . . H
C12 -.0253(2) .1809(10) .03786(11) .0626(11) Uani d . 1 . . C
H12A -.0070 .3007 .0237 .103(19) Uiso calc R 1 . . H
H12B -.0593 .0694 .0187 .078(14) Uiso calc R 1 . . H
C13 -.0650(2) .3139(9) .05824(11) .0587(10) Uani d . 1 . . C
C14 -.0958(3) .4239(12) .07467(14) .0821(15) Uani d . 1 . . C
H14 -.1206 .5125 .0879 .12(2) Uiso calc R 1 . . H
Cl1 .45966(6) 1.0717(2) .18929(4) .0824(4) Uani d . 1 . . Cl
Cl2 .38600(6) 1.48057(19) .14004(3) .0650(3) Uani d . 1 . . Cl
Cl3 .37079(7) 1.4117(2) .21391(3) .0720(3) Uani d . 1 . . Cl
O1 .28681(14) .9747(5) .17708(7) .0529(6) Uani d . 1 . . O
O2 .29272(14) 1.0461(5) .11853(7) .0526(6) Uani d . 1 . . O
C15 .37879(18) 1.2549(6) .17346(11) .0450(8) Uani d . 1 . . C
C16 .31214(17) 1.0752(6) .15390(10) .0401(7) Uani d . 1 . . C
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O .0106 .0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S .1246 .1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl .1484 .1585 '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
C3 S1 C11 103.5(2) y
C4 S2 C12 100.27(19) y
C2 N1 C10 122.7(3) y
C2 N1 H1 115(3) ?
C10 N1 H1 123(3) ?
N1 C2 C3 121.7(3) ?
N1 C2 H2 119.1 ?
C3 C2 H2 119.1 ?
C4 C3 C2 118.1(3) ?
C4 C3 S1 120.9(3) y
C2 C3 S1 120.9(3) y
C3 C4 C5 119.9(3) ?
C3 C4 S2 119.8(3) y
C5 C4 S2 120.3(3) y
C6 C5 C4 124.4(3) ?
C6 C5 C10 117.3(3) ?
C4 C5 C10 118.4(3) ?
C7 C6 C5 121.3(4) ?
C7 C6 H6 119.3 ?
C5 C6 H6 119.3 ?
C6 C7 C8 121.0(4) ?
C6 C7 H7 119.5 ?
C8 C7 H7 119.5 ?
C9 C8 C7 119.7(4) ?
C9 C8 H8 120.1 ?
C7 C8 H8 120.1 ?
C8 C9 C10 120.0(3) ?
C8 C9 H9 120.0 ?
C10 C9 H9 120.0 ?
N1 C10 C9 120.2(3) ?
N1 C10 C5 119.1(3) ?
C9 C10 C5 120.7(3) ?
S1 C11 H11A 109.5 ?
S1 C11 H11B 109.5 ?
H11A C11 H11B 109.5 ?
S1 C11 H11C 109.5 ?
H11A C11 H11C 109.5 ?
H11B C11 H11C 109.5 ?
C13 C12 S2 113.4(3) ?
C13 C12 H12A 108.9 ?
S2 C12 H12A 108.9 ?
C13 C12 H12B 108.9 ?
S2 C12 H12B 108.9 ?
H12A C12 H12B 107.7 ?
C14 C13 C12 178.7(5) ?
C13 C14 H14 180.0 ?
C16 C15 Cl1 107.4(2) ?
C16 C15 Cl3 111.3(2) ?
Cl1 C15 Cl3 109.4(2) ?
C16 C15 Cl2 111.6(2) ?
Cl1 C15 Cl2 108.6(2) ?
Cl3 C15 Cl2 108.39(19) ?
O2 C16 O1 128.6(3) ?
O2 C16 C15 116.5(3) y
O1 C16 C15 114.9(3) y
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 C3 . 1.747(4) y
S1 C11 . 1.773(5) y
S2 C4 . 1.764(3) y
S2 C12 . 1.825(4) y
N1 C2 . 1.312(5) y
N1 C10 . 1.351(4) y
N1 H1 . .91(5) y
C2 C3 . 1.402(5) ?
C2 H2 . .9300 ?
C3 C4 . 1.387(5) ?
C4 C5 . 1.413(5) ?
C5 C6 . 1.407(5) ?
C5 C10 . 1.419(4) ?
C6 C7 . 1.349(5) ?
C6 H6 . .9300 ?
C7 C8 . 1.411(6) ?
C7 H7 . .9300 ?
C8 C9 . 1.359(5) ?
C8 H8 . .9300 ?
C9 C10 . 1.405(5) ?
C9 H9 . .9300 ?
C11 H11A . .9600 ?
C11 H11B . .9600 ?
C11 H11C . .9600 ?
C12 C13 . 1.444(6) ?
C12 H12A . .9700 ?
C12 H12B . .9700 ?
C13 C14 . 1.154(6) y
C14 H14 . .9300 ?
Cl1 C15 . 1.757(4) ?
Cl2 C15 . 1.760(4) ?
Cl3 C15 . 1.759(4) ?
O1 C16 . 1.249(4) y
O2 C16 . 1.219(4) y
C15 C16 . 1.557(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
C10 N1 C2 C3 .2(5) ?
N1 C2 C3 C4 2.7(5) ?
N1 C2 C3 S1 -177.9(3) ?
C11 S1 C3 C4 -169.0(4) ?
C11 S1 C3 C2 11.7(4) y
C2 C3 C4 C5 -3.7(5) ?
S1 C3 C4 C5 177.0(2) ?
C2 C3 C4 S2 178.7(3) ?
S1 C3 C4 S2 -.6(4) y
C12 S2 C4 C3 -75.1(3) y
C12 S2 C4 C5 107.3(3) ?
C3 C4 C5 C6 -177.8(3) ?
S2 C4 C5 C6 -.2(5) ?
C3 C4 C5 C10 1.8(5) ?
S2 C4 C5 C10 179.4(2) ?
C4 C5 C6 C7 178.5(3) ?
C10 C5 C6 C7 -1.1(5) ?
C5 C6 C7 C8 .7(6) ?
C6 C7 C8 C9 .2(6) ?
C7 C8 C9 C10 -.7(6) ?
C2 N1 C10 C9 178.0(3) ?
C2 N1 C10 C5 -2.2(5) ?
C8 C9 C10 N1 -179.9(3) ?
C8 C9 C10 C5 .3(5) ?
C6 C5 C10 N1 -179.3(3) ?
C4 C5 C10 N1 1.1(5) ?
C6 C5 C10 C9 .6(5) ?
C4 C5 C10 C9 -179.0(3) ?
C4 S2 C12 C13 -63.8(4) y
S2 C12 C13 C14 8E1(2) ?
Cl1 C15 C16 O2 -92.3(3) ?
Cl3 C15 C16 O2 147.8(3) ?
Cl2 C15 C16 O2 26.6(4) ?
Cl1 C15 C16 O1 86.0(3) y
Cl3 C15 C16 O1 -33.8(4) ?
Cl2 C15 C16 O1 -155.1(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21135589
