#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/38/4023883.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_4023883
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 H12 N2 S'
_chemical_formula_sum            'C12 H12 N2 S'
_chemical_formula_weight         216.30
_chemical_name_systematic
; 
 ? 
;
_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                 108.291(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.3656(10)
_cell_length_b                   23.557(4)
_cell_length_c                   7.7957(12)
_cell_measurement_reflns_used    3773
_cell_measurement_temperature    90
_cell_measurement_theta_max      28.22
_cell_measurement_theta_min      2.88
_cell_volume                     1109.9(3)
_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 0.998
_diffrn_measured_fraction_theta_max 0.949
_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  0.0539
_diffrn_reflns_av_sigmaI/netI    0.0627
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            6599
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.29
_diffrn_reflns_theta_min         1.73
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.258
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.35
_refine_diff_density_max         0.414
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.075
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         2624
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.0493
_refine_ls_R_factor_gt           0.0446
_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)+(0.0642P)²+0.3478P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1189
_refine_ls_wR_factor_ref         0.1287
_reflns_number_gt                2334
_reflns_number_total             2624
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            jo801996b_si_002_10.cif
_cod_data_source_block           2g
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4023883
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_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 0.3068(3) 0.52435(6) 1.1486(2) 0.0200(3) Uani 1 1 d . . .
H1A H 0.4692 0.5288 1.1998 0.024 Uiso 1 1 calc R . .
H1B H 0.2726 0.5015 1.0367 0.024 Uiso 1 1 calc R . .
C2 C 0.2107(3) 0.49697(6) 1.2854(2) 0.0242(3) Uani 1 1 d . . .
H2A H 0.0722 0.4762 1.2239 0.029 Uiso 1 1 calc R . .
H2B H 0.3179 0.4705 1.3660 0.029 Uiso 1 1 calc R . .
C3 C 0.1664(3) 0.54809(7) 1.3904(2) 0.0269(4) Uani 1 1 d . . .
H3A H 0.3045 0.5615 1.4808 0.032 Uiso 1 1 calc R . .
H3B H 0.0571 0.5387 1.4525 0.032 Uiso 1 1 calc R . .
C4 C 0.0753(3) 0.59229(6) 1.2437(2) 0.0214(3) Uani 1 1 d . . .
H4A H -0.0863 0.5878 1.1868 0.026 Uiso 1 1 calc R . .
H4B H 0.1065 0.6312 1.2928 0.026 Uiso 1 1 calc R . .
C5 C 0.2215(2) 0.61607(6) 0.99145(18) 0.0148(3) Uani 1 1 d . . .
C6 C 0.1003(2) 0.67120(6) 0.97579(18) 0.0153(3) Uani 1 1 d . . .
C7 C -0.1290(2) 0.67184(6) 0.9021(2) 0.0199(3) Uani 1 1 d . . .
H7 H -0.2069 0.6375 0.8604 0.024 Uiso 1 1 calc R . .
C8 C -0.2443(3) 0.72249(6) 0.8894(2) 0.0207(3) Uani 1 1 d . . .
H8 H -0.4008 0.7230 0.8384 0.025 Uiso 1 1 calc R . .
C9 C -0.1295(3) 0.77268(6) 0.95182(19) 0.0192(3) Uani 1 1 d . . .
C10 C 0.1011(3) 0.77247(6) 1.02638(19) 0.0194(3) Uani 1 1 d . . .
H10 H 0.1789 0.8066 1.0696 0.023 Uiso 1 1 calc R . .
C11 C 0.2147(2) 0.72156(6) 1.03636(19) 0.0183(3) Uani 1 1 d . . .
H11 H 0.3715 0.7211 1.0848 0.022 Uiso 1 1 calc R . .
C12 C -0.2520(3) 0.82512(7) 0.9389(2) 0.0236(3) Uani 1 1 d . . .
N1 N 0.1959(2) 0.58012(5) 1.11304(16) 0.0165(3) Uani 1 1 d . . .
N2 N -0.3543(3) 0.86608(6) 0.9260(2) 0.0320(3) Uani 1 1 d . . .
S1 S 0.37029(6) 0.602835(15) 0.85346(5) 0.02061(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 103.53(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 . . ?
C3 C2 C1 102.84(12) . . ?
C3 C2 H2A 111.2 . . ?
C1 C2 H2A 111.2 . . ?
C3 C2 H2B 111.2 . . ?
C1 C2 H2B 111.2 . . ?
H2A C2 H2B 109.1 . . ?
C2 C3 C4 103.12(12) . . ?
C2 C3 H3A 111.1 . . ?
C4 C3 H3A 111.1 . . ?
C2 C3 H3B 111.1 . . ?
C4 C3 H3B 111.1 . . ?
H3A C3 H3B 109.1 . . ?
N1 C4 C3 103.10(12) . . ?
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 116.06(12) . . ?
N1 C5 S1 124.46(11) . . ?
C6 C5 S1 119.45(10) . . ?
C7 C6 C11 119.97(13) . . ?
C7 C6 C5 119.38(12) . . ?
C11 C6 C5 120.64(13) . . ?
C8 C7 C6 120.10(13) . . ?
C8 C7 H7 120.0 . . ?
C6 C7 H7 120.0 . . ?
C9 C8 C7 119.76(14) . . ?
C9 C8 H8 120.1 . . ?
C7 C8 H8 120.1 . . ?
C8 C9 C10 120.57(13) . . ?
C8 C9 C12 119.16(15) . . ?
C10 C9 C12 120.27(14) . . ?
C11 C10 C9 119.09(13) . . ?
C11 C10 H10 120.5 . . ?
C9 C10 H10 120.5 . . ?
C10 C11 C6 120.50(14) . . ?
C10 C11 H11 119.8 . . ?
C6 C11 H11 119.8 . . ?
N2 C12 C9 178.20(19) . . ?
C5 N1 C1 123.15(12) . . ?
C5 N1 C4 125.22(12) . . ?
C1 N1 C4 111.31(11) . . ?
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 1.4760(18) . ?
C1 C2 1.528(2) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.531(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.521(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 N1 1.4829(18) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 N1 1.3189(18) . ?
C5 C6 1.4957(19) . ?
C5 S1 1.6708(14) . ?
C6 C7 1.391(2) . ?
C6 C11 1.3947(19) . ?
C7 C8 1.388(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.395(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.398(2) . ?
C9 C12 1.447(2) . ?
C10 C11 1.390(2) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 N2 1.151(2) . ?
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 -31.42(15) . . . . ?
C1 C2 C3 C4 40.48(16) . . . . ?
C2 C3 C4 N1 -33.33(16) . . . . ?
N1 C5 C6 C7 -70.43(17) . . . . ?
S1 C5 C6 C7 107.52(14) . . . . ?
N1 C5 C6 C11 108.75(15) . . . . ?
S1 C5 C6 C11 -73.30(16) . . . . ?
C11 C6 C7 C8 -0.3(2) . . . . ?
C5 C6 C7 C8 178.91(13) . . . . ?
C6 C7 C8 C9 -0.4(2) . . . . ?
C7 C8 C9 C10 0.3(2) . . . . ?
C7 C8 C9 C12 -179.57(14) . . . . ?
C8 C9 C10 C11 0.5(2) . . . . ?
C12 C9 C10 C11 -179.69(13) . . . . ?
C9 C10 C11 C6 -1.1(2) . . . . ?
C7 C6 C11 C10 1.0(2) . . . . ?
C5 C6 C11 C10 -178.14(13) . . . . ?
C8 C9 C12 N2 -8(5) . . . . ?
C10 C9 C12 N2 172(5) . . . . ?
C6 C5 N1 C1 -178.78(12) . . . . ?
S1 C5 N1 C1 3.4(2) . . . . ?
C6 C5 N1 C4 -5.9(2) . . . . ?
S1 C5 N1 C4 176.29(11) . . . . ?
C2 C1 N1 C5 -175.21(13) . . . . ?
C2 C1 N1 C4 11.01(16) . . . . ?
C3 C4 N1 C5 -159.55(14) . . . . ?
C3 C4 N1 C1 14.08(16) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30658799
