#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/52/2205295.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_2205295
loop_
_publ_author_name
'Vrábel, Viktor'
'Kožíšek, Jozef'
'Marchalín, Štefan'
'Žák, Zdirad'
_publ_section_title
5,6,7,8-Tetrahydro-4aH-thieno[3,2-b]quinolizin-4(10H)-one
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o573
_journal_page_last               o574
_journal_paper_doi               10.1107/S1600536805003454
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C11 H13 N O S'
_chemical_formula_moiety         'C11 H13 N O S'
_chemical_formula_sum            'C11 H13 N O S'
_chemical_formula_weight         207.28
_chemical_name_systematic
;
5,6,7,8-tetrahydro-4aH-thieno[3,2-b]quinolizin-4(10H)-one
;
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 105.84(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.808(2)
_cell_length_b                   18.770(9)
_cell_length_c                   8.256(3)
_cell_measurement_reflns_used    2238
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      34.12
_cell_measurement_theta_min      2.34
_cell_volume                     1014.9(7)
_computing_cell_refinement       'KM-4 Software'
_computing_data_collection       'KM-4 Software (Kuma, 1992)'
_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      298(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Kuma KM-4 CCD'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0340
_diffrn_reflns_av_sigmaI/netI    0.0381
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            8775
_diffrn_reflns_theta_full        27.09
_diffrn_reflns_theta_max         27.09
_diffrn_reflns_theta_min         2.17
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.283
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.403
_refine_diff_density_min         -0.245
_refine_ls_extinction_coef       0.0060(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         2238
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.012
_refine_ls_R_factor_all          0.0524
_refine_ls_R_factor_gt           0.0374
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0629P)²+0.1855P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1026
_refine_ls_wR_factor_ref         0.1137
_reflns_number_gt                1765
_reflns_number_total             2238
_reflns_threshold_expression     F²>2σ(F²)
_cod_data_source_file            kp6040.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2205295
_cod_database_fobs_code          2205295
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_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_type_symbol
C2 0.2977(3) 0.03415(9) 0.1691(2) 0.0562(4) Uani d . 1 C
H2 0.3072 -0.0149 0.1858 0.067 Uiso calc R 1 H
C3 0.1215(3) 0.07026(8) 0.1324(2) 0.0462(4) Uani d . 1 C
H3 -0.0055 0.0494 0.1211 0.055 Uiso calc R 1 H
C4 -0.0034(2) 0.19918(8) 0.05778(18) 0.0373(3) Uani d . 1 C
C5 -0.0812(2) 0.32880(8) 0.0739(2) 0.0441(4) Uani d . 1 C
H5A -0.2122 0.3218 -0.0080 0.053 Uiso calc R 1 H
H5B -0.0994 0.3212 0.1851 0.053 Uiso calc R 1 H
C6 -0.0091(3) 0.40474(9) 0.0610(2) 0.0512(4) Uani d . 1 C
H6A -0.0072 0.4146 -0.0539 0.061 Uiso calc R 1 H
H6B -0.1027 0.4379 0.0909 0.061 Uiso calc R 1 H
C7 0.2027(3) 0.41451(8) 0.1781(2) 0.0537(4) Uani d . 1 C
H7A 0.1971 0.4104 0.2939 0.064 Uiso calc R 1 H
H7B 0.2525 0.4618 0.1628 0.064 Uiso calc R 1 H
C8 0.3481(3) 0.35896(8) 0.1435(2) 0.0475(4) Uani d . 1 C
H8A 0.3627 0.3659 0.0309 0.057 Uiso calc R 1 H
H8B 0.4815 0.3650 0.2227 0.057 Uiso calc R 1 H
C9 0.4245(2) 0.23644(8) 0.1264(2) 0.0398(3) Uani d . 1 C
H9A 0.5553 0.2436 0.2084 0.048 Uiso calc R 1 H
H9B 0.4419 0.2448 0.0151 0.048 Uiso calc R 1 H
C10 0.1524(2) 0.14472(7) 0.11284(17) 0.0360(3) Uani d . 1 C
C11 0.0714(2) 0.27471(7) 0.04268(16) 0.0339(3) Uani d . 1 C
H11 0.0813 0.2813 -0.0726 0.041 Uiso calc R 1 H
C13 0.3526(2) 0.16222(8) 0.13807(17) 0.0370(3) Uani d . 1 C
S1 0.50491(7) 0.08858(2) 0.18172(7) 0.05591(18) Uani d . 1 S
O14 -0.18523(17) 0.18518(7) 0.0166(2) 0.0637(4) Uani d . 1 O
N12 0.27451(17) 0.28635(6) 0.15825(14) 0.0346(3) Uani d . 1 N
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 '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 C2 S1 112.47(13) ?
C3 C2 H2 123.8 ?
S1 C2 H2 123.8 ?
C2 C3 C10 111.71(15) ?
C2 C3 H3 124.1 ?
C10 C3 H3 124.1 ?
O14 C4 C10 122.28(14) ?
O14 C4 C11 120.97(14) ?
C10 C4 C11 116.63(12) ?
C6 C5 C11 111.40(13) yes
C6 C5 H5A 109.3 ?
C11 C5 H5A 109.3 ?
C6 C5 H5B 109.3 ?
C11 C5 H5B 109.3 ?
H5A C5 H5B 108.0 ?
C7 C6 C5 109.77(13) yes
C7 C6 H6A 109.7 ?
C5 C6 H6A 109.7 ?
C7 C6 H6B 109.7 ?
C5 C6 H6B 109.7 ?
H6A C6 H6B 108.2 ?
C6 C7 C8 110.69(14) ?
C6 C7 H7A 109.5 ?
C8 C7 H7A 109.5 ?
C6 C7 H7B 109.5 ?
C8 C7 H7B 109.5 ?
H7A C7 H7B 108.1 ?
N12 C8 C7 111.53(14) ?
N12 C8 H8A 109.3 ?
C7 C8 H8A 109.3 ?
N12 C8 H8B 109.3 ?
C7 C8 H8B 109.3 ?
H8A C8 H8B 108.0 ?
N12 C9 C13 109.25(11) ?
N12 C9 H9A 109.8 ?
C13 C9 H9A 109.8 ?
N12 C9 H9B 109.8 ?
C13 C9 H9B 109.8 ?
H9A C9 H9B 108.3 ?
C13 C10 C3 113.01(13) ?
C13 C10 C4 119.51(13) yes
C3 C10 C4 127.28(13) ?
N12 C11 C4 111.26(11) ?
N12 C11 C5 110.86(12) ?
C4 C11 C5 110.33(11) ?
N12 C11 H11 108.1 ?
C4 C11 H11 108.1 ?
C5 C11 H11 108.1 ?
C10 C13 C9 123.30(13) yes
C10 C13 S1 111.23(11) ?
C9 C13 S1 125.47(11) ?
C13 S1 C2 91.57(8) yes
C9 N12 C11 111.62(11) yes
C9 N12 C8 107.99(12) yes
C11 N12 C8 111.51(12) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C2 C3 1.339(2) ?
C2 S1 1.7214(19) yes
C2 H2 0.9300 ?
C3 C10 1.429(2) ?
C3 H3 0.9300 ?
C4 O14 1.2196(18) ?
C4 C10 1.454(2) yes
C4 C11 1.523(2) ?
C5 C6 1.521(2) ?
C5 C11 1.524(2) ?
C5 H5A 0.9700 ?
C5 H5B 0.9700 ?
C6 C7 1.512(3) ?
C6 H6A 0.9700 ?
C6 H6B 0.9700 ?
C7 C8 1.518(2) ?
C7 H7A 0.9700 ?
C7 H7B 0.9700 ?
C8 N12 1.4687(19) yes
C8 H8A 0.9700 ?
C8 H8B 0.9700 ?
C9 N12 1.4617(18) yes
C9 C13 1.489(2) yes
C9 H9A 0.9700 ?
C9 H9B 0.9700 ?
C10 C13 1.362(2) yes
C11 N12 1.4660(18) yes
C11 H11 0.9800 ?
C13 S1 1.7062(16) 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
S1 C2 C3 C10 0.24(19) ?
C11 C5 C6 C7 -54.44(19) ?
C5 C6 C7 C8 54.5(2) yes
C6 C7 C8 N12 -56.8(2) ?
C2 C3 C10 C13 -0.9(2) ?
C2 C3 C10 C4 173.78(15) ?
O14 C4 C10 C13 172.27(15) ?
C11 C4 C10 C13 -3.84(19) ?
O14 C4 C10 C3 -2.1(2) yes
C11 C4 C10 C3 -178.23(13) ?
O14 C4 C11 N12 156.36(14) ?
C10 C4 C11 N12 -27.47(16) yes
O14 C4 C11 C5 32.89(19) ?
C10 C4 C11 C5 -150.94(13) ?
C6 C5 C11 N12 55.82(17) ?
C6 C5 C11 C4 179.53(13) ?
C3 C10 C13 C9 -179.45(14) ?
C4 C10 C13 C9 5.4(2) ?
C3 C10 C13 S1 1.17(16) ?
C4 C10 C13 S1 -173.98(10) ?
N12 C9 C13 C10 24.4(2) ?
N12 C9 C13 S1 -156.27(11) yes
C10 C13 S1 C2 -0.88(12) ?
C9 C13 S1 C2 179.76(14) yes
C3 C2 S1 C13 0.36(15) ?
C13 C9 N12 C11 -56.30(16) ?
C13 C9 N12 C8 -179.20(12) ?
C4 C11 N12 C9 58.75(14) ?
C5 C11 N12 C9 -178.07(11) ?
C4 C11 N12 C8 179.63(11) ?
C5 C11 N12 C8 -57.20(16) yes
C7 C8 N12 C9 -178.92(14) ?
C7 C8 N12 C11 58.11(18) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9995001
