#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/13/2011304.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_2011304
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 + , Cl - , H2 O'
_chemical_formula_sum            'C13 H14 Cl N O S2'
_chemical_formula_weight         299.85
_chemical_name_systematic
;
 3-Methylthio-4-propargylthioquinolinium chloride monohydrate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_audit_creation_method           SHELXL-97
_cell_angle_alpha                85.72(4)
_cell_angle_beta                 71.16(4)
_cell_angle_gamma                76.94(5)
_cell_formula_units_Z            2
_cell_length_a                   7.571(4)
_cell_length_b                   9.486(6)
_cell_length_c                   10.528(4)
_cell_measurement_reflns_used    39
_cell_measurement_temperature    293
_cell_measurement_theta_max      16.2
_cell_measurement_theta_min      5.1
_cell_volume                     697.1(7)
_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 .985
_diffrn_measured_fraction_theta_max .985
_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  .035
_diffrn_reflns_av_sigmaI/netI    .033
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            3330
_diffrn_reflns_theta_full        27.51
_diffrn_reflns_theta_max         27.51
_diffrn_reflns_theta_min         2.04
_diffrn_standards_decay_%        4
_diffrn_standards_interval_time  90
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    .560
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.428
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             312
_exptl_crystal_size_max          .65
_exptl_crystal_size_mid          .10
_exptl_crystal_size_min          .05
_refine_diff_density_max         .46
_refine_diff_density_min         -.28
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     179
_refine_ls_number_reflns         3149
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          .073
_refine_ls_R_factor_gt           .051
_refine_ls_shift/su_max          .001
_refine_ls_shift/su_mean         .000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0789P)²+0.2963P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         .146
_reflns_number_gt                2429
_reflns_number_total             3149
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            de1147.cif
_cod_data_source_block           II
_cod_depositor_comments
;
 Marking attached hydrogen atoms.

 Antanas Vaitkus,
 2017-03-24
;
_cod_original_cell_volume        697.1(6)
_cod_database_code               2011304
_cod_database_fobs_code          2011304
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
_atom_site_attached_hydrogens
Cl .51162(15) 1.17671(9) .59063(8) .0671(3) Uani d . 1 . . Cl 0
OW1 .1414(6) .0961(4) 1.5305(3) .1142(12) Uani d . 1 . . O 2
S1 .22133(11) .57394(7) .84116(7) .0489(2) Uani d . 1 . . S 0
S2 .10128(11) .67154(9) 1.13383(7) .0505(2) Uani d . 1 . . S 0
N1 .3469(3) .9640(2) .7999(2) .0388(5) Uani d . 1 . . N 0
H1 .389(5) 1.019(4) .730(4) .059(9) Uiso d . 1 . . H 0
C2 .3278(4) .8362(3) .7718(3) .0404(5) Uani d . 1 . . C 0
H2 .3650 .8074 .6828 .068(10) Uiso calc R 1 . . H 0
C3 .2524(3) .7437(3) .8740(3) .0365(5) Uani d . 1 . . C 0
C4 .1989(3) .7888(3) 1.0061(2) .0355(5) Uani d . 1 . . C 0
C5 .2159(3) .9282(3) 1.0348(2) .0357(5) Uani d . 1 . . C 0
C6 .1564(4) .9872(3) 1.1653(3) .0442(6) Uani d . 1 . . C 0
H6 .1020 .9334 1.2393 .043(7) Uiso calc R 1 . . H 0
C7 .1781(4) 1.1217(3) 1.1832(3) .0518(7) Uani d . 1 . . C 0
H7 .1402 1.1580 1.2698 .065(10) Uiso calc R 1 . . H 0
C8 .2563(4) 1.2073(3) 1.0742(3) .0501(7) Uani d . 1 . . C 0
H8 .2699 1.2991 1.0889 .062(10) Uiso calc R 1 . . H 0
C9 .3123(4) 1.1559(3) .9471(3) .0431(6) Uani d . 1 . . C 0
H9 .3630 1.2127 .8745 .062(10) Uiso calc R 1 . . H 0
C10 .2930(3) 1.0161(3) .9261(2) .0356(5) Uani d . 1 . . C 0
C11 .2826(5) .5702(4) .6626(3) .0581(8) Uani d . 1 . . C 0
H11A .1966 .6466 .6339 .060(10) Uiso calc R 1 . . H 0
H11B .2730 .4787 .6352 .082(12) Uiso calc R 1 . . H 0
H11C .4111 .5834 .6227 .082(12) Uiso calc R 1 . . H 0
C12 .2750(7) .6326(5) 1.2213(5) .0879(15) Uani d . 1 . . C 0
H12A .4030 .6110 1.1578 .19(3) Uiso calc R 1 . . H 0
H12B .2634 .7155 1.2744 .21(4) Uiso calc R 1 . . H 0
C13 .2397(5) .5092(3) 1.3075(3) .0572(8) Uani d . 1 . . C 0
C14 .2087(5) .4110(4) 1.3768(3) .0629(8) Uani d . 1 . . C 0
H14 .1838 .3322 1.4325 .090(13) Uiso calc R 1 . . H 0
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 103.84(14) y
C4 S2 C12 101.79(16) y
C2 N1 C10 123.7(2) y
C2 N1 H1 116(2) ?
C10 N1 H1 120(2) ?
N1 C2 C3 120.8(2) ?
N1 C2 H2 119.6 ?
C3 C2 H2 119.6 ?
C4 C3 C2 118.5(2) ?
C4 C3 S1 119.23(19) y
C2 C3 S1 122.3(2) y
C3 C4 C5 120.1(2) ?
C3 C4 S2 117.91(19) y
C5 C4 S2 121.89(19) y
C10 C5 C6 117.3(2) ?
C10 C5 C4 118.2(2) ?
C6 C5 C4 124.5(2) ?
C7 C6 C5 120.5(3) ?
C7 C6 H6 119.8 ?
C5 C6 H6 119.8 ?
C6 C7 C8 121.5(3) ?
C6 C7 H7 119.2 ?
C8 C7 H7 119.2 ?
C9 C8 C7 120.0(3) ?
C9 C8 H8 120.0 ?
C7 C8 H8 120.0 ?
C8 C9 C10 119.5(3) ?
C8 C9 H9 120.2 ?
C10 C9 H9 120.2 ?
N1 C10 C9 120.1(2) ?
N1 C10 C5 118.7(2) ?
C9 C10 C5 121.2(2) ?
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 107.7(2) ?
C13 C12 H12A 110.2 ?
S2 C12 H12A 110.2 ?
C13 C12 H12B 110.2 ?
S2 C12 H12B 110.2 ?
H12A C12 H12B 108.5 ?
C14 C13 C12 179.0(4) ?
C13 C14 H14 180.0 ?
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 . 1.753(3) y
S1 C11 . 1.786(3) y
S2 C4 . 1.760(3) y
S2 C12 . 1.796(4) y
N1 C2 . 1.319(3) y
N1 C10 . 1.355(3) y
N1 H1 . .88(4) y
C2 C3 . 1.394(4) ?
C2 H2 . .9300 ?
C3 C4 . 1.388(4) ?
C4 C5 . 1.421(3) ?
C5 C10 . 1.411(3) ?
C5 C6 . 1.416(4) ?
C6 C7 . 1.357(4) ?
C6 H6 . .9300 ?
C7 C8 . 1.402(5) ?
C7 H7 . .9300 ?
C8 C9 . 1.358(4) ?
C8 H8 . .9300 ?
C9 C10 . 1.408(4) ?
C9 H9 . .9300 ?
C11 H11A . .9600 ?
C11 H11B . .9600 ?
C11 H11C . .9600 ?
C12 C13 . 1.446(5) ?
C12 H12A . .9700 ?
C12 H12B . .9700 ?
C13 C14 . 1.159(4) y
C14 H14 . .9300 ?
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 -1.4(4) ?
N1 C2 C3 C4 -.3(4) ?
N1 C2 C3 S1 179.1(2) ?
C11 S1 C3 C4 173.8(2) ?
C11 S1 C3 C2 -5.6(3) y
C2 C3 C4 C5 1.9(4) ?
S1 C3 C4 C5 -177.52(18) ?
C2 C3 C4 S2 179.21(19) ?
S1 C3 C4 S2 -.2(3) y
C12 S2 C4 C3 116.8(3) y
C12 S2 C4 C5 -65.9(3) ?
C3 C4 C5 C10 -1.8(3) ?
S2 C4 C5 C10 -178.97(18) ?
C3 C4 C5 C6 176.6(2) ?
S2 C4 C5 C6 -.6(4) ?
C10 C5 C6 C7 -1.6(4) ?
C4 C5 C6 C7 -179.9(3) ?
C5 C6 C7 C8 1.1(4) ?
C6 C7 C8 C9 .0(5) ?
C7 C8 C9 C10 -.7(4) ?
C2 N1 C10 C9 -177.8(2) ?
C2 N1 C10 C5 1.5(4) ?
C8 C9 C10 N1 179.5(2) ?
C8 C9 C10 C5 .2(4) ?
C6 C5 C10 N1 -178.4(2) ?
C4 C5 C10 N1 .1(3) ?
C6 C5 C10 C9 .9(4) ?
C4 C5 C10 C9 179.4(2) ?
C4 S2 C12 C13 -165.5(3) y
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30652303
