#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/38/4023882.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_4023882
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_formula_moiety         'C12 H15 N S'
_chemical_formula_sum            'C12 H15 N S'
_chemical_formula_weight         205.31
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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            8
_cell_length_a                   14.5885(18)
_cell_length_b                   8.2099(10)
_cell_length_c                   18.071(2)
_cell_measurement_reflns_used    2715
_cell_measurement_temperature    90
_cell_measurement_theta_max      28.20
_cell_measurement_theta_min      2.25
_cell_volume                     2164.3(5)
_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 0.999
_diffrn_measured_fraction_theta_max 0.976
_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  0.0585
_diffrn_reflns_av_sigmaI/netI    0.0501
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            12277
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.29
_diffrn_reflns_theta_min         2.25
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.258
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.260
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             880
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.391
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         2618
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0595
_refine_ls_R_factor_gt           0.0410
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0485P)²+1.4903P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0992
_refine_ls_wR_factor_ref         0.1138
_reflns_number_gt                1981
_reflns_number_total             2618
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            jo801996b_si_002_09.cif
_cod_data_source_block           2d
_cod_database_code               4023882
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'
'-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 0.64656(11) 0.3238(2) 0.69880(10) 0.0168(4) Uani 1 1 d . . .
H1A H 0.6905 0.2635 0.6673 0.020 Uiso 1 1 calc R . .
H1B H 0.6406 0.2668 0.7468 0.020 Uiso 1 1 calc R . .
C2 C 0.67749(12) 0.4995(2) 0.70994(10) 0.0196(4) Uani 1 1 d . . .
H2A H 0.6557 0.5428 0.7580 0.024 Uiso 1 1 calc R . .
H2B H 0.7451 0.5085 0.7078 0.024 Uiso 1 1 calc R . .
C3 C 0.63266(12) 0.5893(2) 0.64519(10) 0.0195(4) Uani 1 1 d . . .
H3A H 0.6276 0.7074 0.6554 0.023 Uiso 1 1 calc R . .
H3B H 0.6677 0.5731 0.5989 0.023 Uiso 1 1 calc R . .
C4 C 0.53831(12) 0.51010(19) 0.64046(10) 0.0171(4) Uani 1 1 d . . .
H4A H 0.4946 0.5622 0.6751 0.020 Uiso 1 1 calc R . .
H4B H 0.5134 0.5165 0.5896 0.020 Uiso 1 1 calc R . .
C5 C 0.50745(12) 0.2098(2) 0.64362(9) 0.0139(3) Uani 1 1 d . . .
C6 C 0.41644(12) 0.23657(19) 0.60841(9) 0.0144(3) Uani 1 1 d . . .
C7 C 0.34715(12) 0.3233(2) 0.64481(9) 0.0166(4) Uani 1 1 d . . .
H7 H 0.3603 0.3790 0.6896 0.020 Uiso 1 1 calc R . .
C8 C 0.25911(12) 0.3279(2) 0.61546(9) 0.0170(4) Uani 1 1 d . . .
H8 H 0.2125 0.3865 0.6408 0.020 Uiso 1 1 calc R . .
C9 C 0.23788(11) 0.24816(19) 0.54953(9) 0.0150(3) Uani 1 1 d . . .
C10 C 0.30859(12) 0.16930(19) 0.51195(9) 0.0160(3) Uani 1 1 d . . .
H10 H 0.2962 0.1195 0.4656 0.019 Uiso 1 1 calc R . .
C11 C 0.39620(12) 0.16209(19) 0.54072(9) 0.0155(3) Uani 1 1 d . . .
H11 H 0.4430 0.1062 0.5144 0.019 Uiso 1 1 calc R . .
C12 C 0.14097(12) 0.2441(2) 0.52053(10) 0.0198(4) Uani 1 1 d . . .
H12A H 0.1378 0.3040 0.4737 0.024 Uiso 1 1 calc R . .
H12B H 0.0998 0.2948 0.5567 0.024 Uiso 1 1 calc R . .
H12C H 0.1223 0.1308 0.5124 0.024 Uiso 1 1 calc R . .
N1 N 0.55695(9) 0.33880(16) 0.66204(8) 0.0143(3) Uani 1 1 d . . .
S1 S 0.54277(3) 0.01755(5) 0.65933(2) 0.01740(14) 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'
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 104.09(13) . . ?
N1 C1 H1A 110.9 . . ?
C2 C1 H1A 110.9 . . ?
N1 C1 H1B 110.9 . . ?
C2 C1 H1B 110.9 . . ?
H1A C1 H1B 109.0 . . ?
C3 C2 C1 103.20(14) . . ?
C3 C2 H2A 111.1 . . ?
C1 C2 H2A 111.1 . . ?
C3 C2 H2B 111.1 . . ?
C1 C2 H2B 111.1 . . ?
H2A C2 H2B 109.1 . . ?
C4 C3 C2 102.91(14) . . ?
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 102.94(13) . . ?
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 118.40(14) . . ?
N1 C5 S1 122.71(13) . . ?
C6 C5 S1 118.89(12) . . ?
C11 C6 C7 118.72(15) . . ?
C11 C6 C5 119.83(15) . . ?
C7 C6 C5 121.19(15) . . ?
C8 C7 C6 120.09(16) . . ?
C8 C7 H7 120.0 . . ?
C6 C7 H7 120.0 . . ?
C9 C8 C7 121.24(16) . . ?
C9 C8 H8 119.4 . . ?
C7 C8 H8 119.4 . . ?
C8 C9 C10 118.02(15) . . ?
C8 C9 C12 121.04(15) . . ?
C10 C9 C12 120.93(15) . . ?
C11 C10 C9 121.41(16) . . ?
C11 C10 H10 119.3 . . ?
C9 C10 H10 119.3 . . ?
C10 C11 C6 120.38(15) . . ?
C10 C11 H11 119.8 . . ?
C6 C11 H11 119.8 . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C5 N1 C1 122.07(14) . . ?
C5 N1 C4 126.29(14) . . ?
C1 N1 C4 111.13(13) . . ?
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 1.472(2) . ?
C1 C2 1.525(2) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.530(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.525(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 N1 1.485(2) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 N1 1.324(2) . ?
C5 C6 1.489(2) . ?
C5 S1 1.6844(17) . ?
C6 C11 1.399(2) . ?
C6 C7 1.401(2) . ?
C7 C8 1.390(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.394(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.394(2) . ?
C9 C12 1.508(2) . ?
C10 C11 1.381(2) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
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 -29.60(17) . . . . ?
C1 C2 C3 C4 39.80(17) . . . . ?
C2 C3 C4 N1 -34.20(17) . . . . ?
N1 C5 C6 C11 125.92(17) . . . . ?
S1 C5 C6 C11 -54.8(2) . . . . ?
N1 C5 C6 C7 -59.9(2) . . . . ?
S1 C5 C6 C7 119.40(16) . . . . ?
C11 C6 C7 C8 3.0(2) . . . . ?
C5 C6 C7 C8 -171.24(15) . . . . ?
C6 C7 C8 C9 -0.4(3) . . . . ?
C7 C8 C9 C10 -2.8(2) . . . . ?
C7 C8 C9 C12 175.89(16) . . . . ?
C8 C9 C10 C11 3.5(2) . . . . ?
C12 C9 C10 C11 -175.20(15) . . . . ?
C9 C10 C11 C6 -0.9(2) . . . . ?
C7 C6 C11 C10 -2.3(2) . . . . ?
C5 C6 C11 C10 171.99(15) . . . . ?
C6 C5 N1 C1 178.39(15) . . . . ?
S1 C5 N1 C1 -0.9(2) . . . . ?
C6 C5 N1 C4 -10.6(2) . . . . ?
S1 C5 N1 C4 170.12(13) . . . . ?
C2 C1 N1 C5 -179.41(15) . . . . ?
C2 C1 N1 C4 8.35(18) . . . . ?
C3 C4 N1 C5 -155.49(16) . . . . ?
C3 C4 N1 C1 16.34(18) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 16784775
