#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/38/4023881.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4023881
loop_
_publ_author_name
'Tetsuharu Hori'
'Yuko Otani'
'Masatoshi Kawahata'
'Kentaro Yamaguchi'
'Tomohiko Ohwada'
_publ_section_title
;
 Nonplanar Structures of Thioamides Derived from
 7-Azabicyclo[2.2.1]heptane. Electronically Tunable
 Planarity of Thioamides
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              9102
_journal_page_last               9108
_journal_paper_doi               10.1021/jo801996b
_journal_volume                  73
_journal_year                    2008
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C12 H15 N O S'
_chemical_formula_sum            'C12 H15 N O S'
_chemical_formula_weight         221.31
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.6481(11)
_cell_length_b                   13.449(3)
_cell_length_c                   14.691(3)
_cell_measurement_reflns_used    3291
_cell_measurement_temperature    90
_cell_measurement_theta_max      27.98
_cell_measurement_theta_min      2.77
_cell_volume                     1116.0(4)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        'SAINT (Bruker, 1998)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      90
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device_type  'Bruker SMART 1000 CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_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  0.0380
_diffrn_reflns_av_sigmaI/netI    0.0436
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6818
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         2.77
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.262
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.248
_refine_diff_density_min         -0.176
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.07(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         2608
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0343
_refine_ls_R_factor_gt           0.0315
_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)+(0.0331P)²+0.2246P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0778
_refine_ls_wR_factor_ref         0.0790
_reflns_number_gt                2444
_reflns_number_total             2608
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            jo801996b_si_002_08.cif
_cod_data_source_block           2c
_cod_database_code               4023881
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5825(3) 0.32171(12) 0.09386(10) 0.0212(3) Uani 1 1 d . . .
H1A H 0.4342 0.3587 0.0819 0.025 Uiso 1 1 calc R . .
H1B H 0.5936 0.2651 0.0510 0.025 Uiso 1 1 calc R . .
C2 C 0.7971(3) 0.38947(12) 0.08557(10) 0.0200(3) Uani 1 1 d . . .
H2A H 0.7694 0.4425 0.0401 0.024 Uiso 1 1 calc R . .
H2B H 0.9399 0.3513 0.0680 0.024 Uiso 1 1 calc R . .
C3 C 0.8230(3) 0.43300(12) 0.18134(10) 0.0224(4) Uani 1 1 d . . .
H3A H 0.9851 0.4586 0.1916 0.027 Uiso 1 1 calc R . .
H3B H 0.7079 0.4873 0.1917 0.027 Uiso 1 1 calc R . .
C4 C 0.7708(3) 0.34395(11) 0.24252(10) 0.0172(3) Uani 1 1 d . . .
H4A H 0.9152 0.3039 0.2531 0.021 Uiso 1 1 calc R . .
H4B H 0.7056 0.3655 0.3019 0.021 Uiso 1 1 calc R . .
C5 C 0.4483(3) 0.21843(11) 0.22243(10) 0.0143(3) Uani 1 1 d . . .
C6 C 0.4908(3) 0.18540(11) 0.31852(9) 0.0141(3) Uani 1 1 d . . .
C7 C 0.6969(3) 0.13462(11) 0.34148(10) 0.0153(3) Uani 1 1 d . . .
H7 H 0.8186 0.1275 0.2973 0.018 Uiso 1 1 calc R . .
C8 C 0.7286(3) 0.09387(10) 0.42819(9) 0.0152(3) Uani 1 1 d . . .
H8 H 0.8681 0.0575 0.4423 0.018 Uiso 1 1 calc R . .
C9 C 0.5532(3) 0.10729(11) 0.49360(10) 0.0152(3) Uani 1 1 d . . .
C10 C 0.3498(3) 0.16160(12) 0.47284(10) 0.0165(3) Uani 1 1 d . . .
H10 H 0.2337 0.1731 0.5184 0.020 Uiso 1 1 calc R . .
C11 C 0.3172(3) 0.19879(11) 0.38573(10) 0.0148(3) Uani 1 1 d . . .
H11 H 0.1759 0.2337 0.3714 0.018 Uiso 1 1 calc R . .
C12 C 0.7625(4) 0.00992(13) 0.60325(10) 0.0233(3) Uani 1 1 d . . .
H12A H 0.9091 0.0477 0.5944 0.028 Uiso 1 1 calc R . .
H12B H 0.7637 -0.0488 0.5638 0.028 Uiso 1 1 calc R . .
H12C H 0.7508 -0.0111 0.6670 0.028 Uiso 1 1 calc R . .
N1 N 0.5927(2) 0.28711(9) 0.18950(8) 0.0152(3) Uani 1 1 d . . .
O1 O 0.5642(2) 0.07111(8) 0.58084(7) 0.0197(2) Uani 1 1 d . . .
S1 S 0.23199(7) 0.16507(3) 0.16163(2) 0.01961(11) Uani 1 1 d . . .
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'
N N 0.0061 0.0033 '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'
S S 0.1246 0.1234 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 103.49(12) . . ?
N1 C1 H1A 111.1 . . ?
C2 C1 H1A 111.1 . . ?
N1 C1 H1B 111.1 . . ?
C2 C1 H1B 111.1 . . ?
H1A C1 H1B 109.0 . . ?
C1 C2 C3 103.39(13) . . ?
C1 C2 H2A 111.1 . . ?
C3 C2 H2A 111.1 . . ?
C1 C2 H2B 111.1 . . ?
C3 C2 H2B 111.1 . . ?
H2A C2 H2B 109.0 . . ?
C4 C3 C2 102.87(12) . . ?
C4 C3 H3A 111.2 . . ?
C2 C3 H3A 111.2 . . ?
C4 C3 H3B 111.2 . . ?
C2 C3 H3B 111.2 . . ?
H3A C3 H3B 109.1 . . ?
N1 C4 C3 103.07(11) . . ?
N1 C4 H4A 111.2 . . ?
C3 C4 H4A 111.2 . . ?
N1 C4 H4B 111.2 . . ?
C3 C4 H4B 111.2 . . ?
H4A C4 H4B 109.1 . . ?
N1 C5 C6 116.88(13) . . ?
N1 C5 S1 123.61(11) . . ?
C6 C5 S1 119.47(11) . . ?
C7 C6 C11 118.49(13) . . ?
C7 C6 C5 120.52(13) . . ?
C11 C6 C5 120.84(13) . . ?
C6 C7 C8 121.38(13) . . ?
C6 C7 H7 119.3 . . ?
C8 C7 H7 119.3 . . ?
C9 C8 C7 119.13(14) . . ?
C9 C8 H8 120.4 . . ?
C7 C8 H8 120.4 . . ?
O1 C9 C8 124.51(14) . . ?
O1 C9 C10 115.29(13) . . ?
C8 C9 C10 120.20(13) . . ?
C11 C10 C9 120.02(14) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C10 C11 C6 120.69(14) . . ?
C10 C11 H11 119.7 . . ?
C6 C11 H11 119.7 . . ?
O1 C12 H12A 109.5 . . ?
O1 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O1 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C5 N1 C1 122.82(13) . . ?
C5 N1 C4 125.82(12) . . ?
C1 N1 C4 111.23(12) . . ?
C9 O1 C12 117.07(12) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.4813(18) . ?
C1 C2 1.521(2) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.531(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.526(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 N1 1.4842(19) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 N1 1.324(2) . ?
C5 C6 1.4993(19) . ?
C5 S1 1.6750(16) . ?
C6 C7 1.391(2) . ?
C6 C11 1.403(2) . ?
C7 C8 1.398(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.392(2) . ?
C8 H8 0.9500 . ?
C9 O1 1.3722(18) . ?
C9 C10 1.395(2) . ?
C10 C11 1.386(2) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 O1 1.429(2) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 -31.18(15) . . . . ?
C1 C2 C3 C4 40.36(16) . . . . ?
C2 C3 C4 N1 -33.24(16) . . . . ?
N1 C5 C6 C7 -65.89(18) . . . . ?
S1 C5 C6 C7 111.88(15) . . . . ?
N1 C5 C6 C11 118.57(16) . . . . ?
S1 C5 C6 C11 -63.65(17) . . . . ?
C11 C6 C7 C8 2.6(2) . . . . ?
C5 C6 C7 C8 -173.03(13) . . . . ?
C6 C7 C8 C9 -2.1(2) . . . . ?
C7 C8 C9 O1 -179.89(14) . . . . ?
C7 C8 C9 C10 -0.7(2) . . . . ?
O1 C9 C10 C11 -177.92(13) . . . . ?
C8 C9 C10 C11 2.8(2) . . . . ?
C9 C10 C11 C6 -2.2(2) . . . . ?
C7 C6 C11 C10 -0.5(2) . . . . ?
C5 C6 C11 C10 175.17(14) . . . . ?
C6 C5 N1 C1 175.62(13) . . . . ?
S1 C5 N1 C1 -2.0(2) . . . . ?
C6 C5 N1 C4 -8.9(2) . . . . ?
S1 C5 N1 C4 173.47(12) . . . . ?
C2 C1 N1 C5 -173.33(14) . . . . ?
C2 C1 N1 C4 10.58(17) . . . . ?
C3 C4 N1 C5 -161.60(15) . . . . ?
C3 C4 N1 C1 14.36(17) . . . . ?
C8 C9 O1 C12 -4.5(2) . . . . ?
C10 C9 O1 C12 176.25(13) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 726217
