#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/38/4023880.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_4023880
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         'C11 H13 N S'
_chemical_formula_sum            'C11 H13 N S'
_chemical_formula_weight         191.28
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 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                   18.069(4)
_cell_length_b                   5.9249(14)
_cell_length_c                   9.399(2)
_cell_measurement_reflns_used    2749
_cell_measurement_temperature    150
_cell_measurement_theta_max      27.52
_cell_measurement_theta_min      3.13
_cell_volume                     1006.3(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      150
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.977
_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  0.0465
_diffrn_reflns_av_sigmaI/netI    0.0570
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            5558
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.25
_diffrn_reflns_theta_min         2.25
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.273
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.263
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.319
_refine_diff_density_min         -0.156
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     118
_refine_ls_number_reflns         2247
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.082
_refine_ls_R_factor_all          0.0412
_refine_ls_R_factor_gt           0.0376
_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)+(0.0566P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1002
_refine_ls_wR_factor_ref         0.1023
_reflns_number_gt                2065
_reflns_number_total             2247
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            jo801996b_si_002_07.cif
_cod_data_source_block           2a
_cod_database_code               4023880
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y+1/2, z+1/2'
'x+1/2, -y+1/2, z'
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 -0.08145(10) -0.2786(3) 0.2981(2) 0.0295(4) Uani 1 1 d . . .
H1A H -0.0764 -0.2693 0.1934 0.035 Uiso 1 1 calc R . .
H1B H -0.1044 -0.1376 0.3335 0.035 Uiso 1 1 calc R . .
C2 C -0.12661(11) -0.4835(3) 0.3413(2) 0.0321(4) Uani 1 1 d . . .
H2A H -0.1179 -0.6118 0.2760 0.039 Uiso 1 1 calc R . .
H2B H -0.1802 -0.4485 0.3434 0.039 Uiso 1 1 calc R . .
C3 C -0.09707(11) -0.5341(3) 0.4908(2) 0.0310(4) Uani 1 1 d . . .
H3A H -0.1186 -0.4299 0.5619 0.037 Uiso 1 1 calc R . .
H3B H -0.1081 -0.6915 0.5191 0.037 Uiso 1 1 calc R . .
C4 C -0.01415(10) -0.4969(3) 0.4758(2) 0.0254(4) Uani 1 1 d . . .
H4A H 0.0079 -0.4465 0.5668 0.031 Uiso 1 1 calc R . .
H4B H 0.0111 -0.6365 0.4441 0.031 Uiso 1 1 calc R . .
C5 C 0.04942(9) -0.1898(3) 0.33965(19) 0.0232(4) Uani 1 1 d . . .
C6 C 0.11961(9) -0.2494(3) 0.4153(2) 0.0234(4) Uani 1 1 d . . .
C7 C 0.15221(10) -0.0920(3) 0.5047(2) 0.0290(4) Uani 1 1 d . . .
H7 H 0.1303 0.0527 0.5161 0.035 Uiso 1 1 calc R . .
C8 C 0.21666(11) -0.1451(4) 0.5777(2) 0.0352(5) Uani 1 1 d . . .
H8 H 0.2381 -0.0376 0.6403 0.042 Uiso 1 1 calc R . .
C9 C 0.24999(10) -0.3545(4) 0.5598(2) 0.0362(5) Uani 1 1 d . . .
H9 H 0.2939 -0.3911 0.6105 0.043 Uiso 1 1 calc R . .
C10 C 0.21876(11) -0.5087(3) 0.4678(3) 0.0341(5) Uani 1 1 d . . .
H10 H 0.2422 -0.6503 0.4529 0.041 Uiso 1 1 calc R . .
C11 C 0.15321(10) -0.4588(3) 0.3964(2) 0.0285(4) Uani 1 1 d . . .
H11 H 0.1315 -0.5674 0.3350 0.034 Uiso 1 1 calc R . .
N1 N -0.00915(8) -0.3177(2) 0.36609(17) 0.0231(3) Uani 1 1 d . . .
S1 S 0.04739(3) 0.02957(7) 0.22672(6) 0.03311(15) 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 103.57(14) . . ?
N1 C1 H1A 111.0 . . ?
C2 C1 H1A 111.0 . . ?
N1 C1 H1B 111.0 . . ?
C2 C1 H1B 111.0 . . ?
H1A C1 H1B 109.0 . . ?
C1 C2 C3 102.38(16) . . ?
C1 C2 H2A 111.3 . . ?
C3 C2 H2A 111.3 . . ?
C1 C2 H2B 111.3 . . ?
C3 C2 H2B 111.3 . . ?
H2A C2 H2B 109.2 . . ?
C4 C3 C2 103.28(16) . . ?
C4 C3 H3A 111.1 . . ?
C2 C3 H3A 111.1 . . ?
C4 C3 H3B 111.1 . . ?
C2 C3 H3B 111.1 . . ?
H3A C3 H3B 109.1 . . ?
N1 C4 C3 103.18(14) . . ?
N1 C4 H4A 111.1 . . ?
C3 C4 H4A 111.1 . . ?
N1 C4 H4B 111.1 . . ?
C3 C4 H4B 111.1 . . ?
H4A C4 H4B 109.1 . . ?
N1 C5 C6 116.91(15) . . ?
N1 C5 S1 122.96(13) . . ?
C6 C5 S1 120.13(13) . . ?
C7 C6 C11 119.42(17) . . ?
C7 C6 C5 119.29(16) . . ?
C11 C6 C5 121.29(16) . . ?
C6 C7 C8 120.21(18) . . ?
C6 C7 H7 119.9 . . ?
C8 C7 H7 119.9 . . ?
C9 C8 C7 120.45(19) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
C8 C9 C10 119.35(19) . . ?
C8 C9 H9 120.3 . . ?
C10 C9 H9 120.3 . . ?
C11 C10 C9 120.62(18) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C10 C11 C6 119.91(18) . . ?
C10 C11 H11 120.0 . . ?
C6 C11 H11 120.0 . . ?
C5 N1 C4 126.05(15) . . ?
C5 N1 C1 122.47(15) . . ?
C4 N1 C1 111.14(14) . . ?
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 1.473(2) . ?
C1 C2 1.518(3) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.533(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.521(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 N1 1.483(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 N1 1.325(2) . ?
C5 C6 1.496(2) . ?
C5 S1 1.6784(19) . ?
C6 C7 1.387(2) . ?
C6 C11 1.393(2) . ?
C7 C8 1.388(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.389(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.379(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.393(3) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
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 33.92(18) . . . . ?
C1 C2 C3 C4 -40.83(18) . . . . ?
C2 C3 C4 N1 31.40(18) . . . . ?
N1 C5 C6 C7 -120.00(19) . . . . ?
S1 C5 C6 C7 60.3(2) . . . . ?
N1 C5 C6 C11 60.7(2) . . . . ?
S1 C5 C6 C11 -118.97(18) . . . . ?
C11 C6 C7 C8 -1.8(3) . . . . ?
C5 C6 C7 C8 178.96(18) . . . . ?
C6 C7 C8 C9 1.3(3) . . . . ?
C7 C8 C9 C10 0.6(3) . . . . ?
C8 C9 C10 C11 -2.0(3) . . . . ?
C9 C10 C11 C6 1.5(3) . . . . ?
C7 C6 C11 C10 0.4(3) . . . . ?
C5 C6 C11 C10 179.63(18) . . . . ?
C6 C5 N1 C4 7.7(3) . . . . ?
S1 C5 N1 C4 -172.60(16) . . . . ?
C6 C5 N1 C1 -179.58(17) . . . . ?
S1 C5 N1 C1 0.1(2) . . . . ?
C3 C4 N1 C5 162.97(16) . . . . ?
C3 C4 N1 C1 -10.45(19) . . . . ?
C2 C1 N1 C5 171.35(16) . . . . ?
C2 C1 N1 C4 -15.0(2) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 526433
