#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:02:44 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178417 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/38/4023879.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_4023879
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         'C13 H14 N2 O2 S'
_chemical_formula_sum            'C13 H14 N2 O2 S'
_chemical_formula_weight         262.32
_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                 98.845(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.9612(16)
_cell_length_b                   6.8315(14)
_cell_length_c                   23.039(5)
_cell_measurement_reflns_used    3767
_cell_measurement_temperature    90
_cell_measurement_theta_max      28.26
_cell_measurement_theta_min      2.59
_cell_volume                     1238.1(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_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.961
_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  0.0386
_diffrn_reflns_av_sigmaI/netI    0.0435
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            7277
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.26
_diffrn_reflns_theta_min         1.79
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.257
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.330
_refine_diff_density_min         -0.286
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2935
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0402
_refine_ls_R_factor_gt           0.0348
_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)+(0.0437P)²+0.4673P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0924
_refine_ls_wR_factor_ref         0.0970
_reflns_number_gt                2570
_reflns_number_total             2935
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            jo801996b_si_002_06.cif
_cod_data_source_block           1h
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4023879
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 -0.30523(16) 0.4104(2) 0.19633(6) 0.0176(3) Uani 1 1 d . . .
H1 H -0.2408 0.3225 0.2266 0.021 Uiso 1 1 calc R . .
C2 C -0.41793(17) 0.5643(2) 0.22034(6) 0.0195(3) Uani 1 1 d . . .
H2A H -0.3624 0.6163 0.2586 0.023 Uiso 1 1 calc R . .
H2B H -0.5298 0.5084 0.2251 0.023 Uiso 1 1 calc R . .
C3 C -0.43736(16) 0.7263(2) 0.17236(6) 0.0194(3) Uani 1 1 d . . .
H3A H -0.5582 0.7468 0.1556 0.023 Uiso 1 1 calc R . .
H3B H -0.3882 0.8519 0.1883 0.023 Uiso 1 1 calc R . .
C4 C -0.33674(15) 0.6426(2) 0.12615(5) 0.0164(3) Uani 1 1 d . . .
H4 H -0.2976 0.7417 0.0992 0.020 Uiso 1 1 calc R . .
C5 C -0.43358(17) 0.4673(2) 0.09540(6) 0.0212(3) Uani 1 1 d . . .
H5A H -0.3845 0.4268 0.0603 0.025 Uiso 1 1 calc R . .
H5B H -0.5555 0.4984 0.0835 0.025 Uiso 1 1 calc R . .
C6 C -0.40873(18) 0.3053(2) 0.14364(6) 0.0227(3) Uani 1 1 d . . .
H6A H -0.5194 0.2595 0.1531 0.027 Uiso 1 1 calc R . .
H6B H -0.3455 0.1920 0.1311 0.027 Uiso 1 1 calc R . .
C7 C -0.03288(15) 0.54427(18) 0.16765(5) 0.0142(2) Uani 1 1 d . . .
C8 C 0.03545(14) 0.68291(19) 0.12663(5) 0.0140(2) Uani 1 1 d . . .
C9 C 0.08545(16) 0.60730(19) 0.07568(6) 0.0167(3) Uani 1 1 d . . .
H9 H 0.0704 0.4720 0.0669 0.020 Uiso 1 1 calc R . .
C10 C 0.15697(16) 0.7283(2) 0.03782(5) 0.0172(3) Uani 1 1 d . . .
H10 H 0.1907 0.6779 0.0030 0.021 Uiso 1 1 calc R . .
C11 C 0.17792(15) 0.92433(19) 0.05211(5) 0.0148(3) Uani 1 1 d . . .
C12 C 0.12931(16) 1.0042(2) 0.10228(5) 0.0172(3) Uani 1 1 d . . .
H12 H 0.1454 1.1395 0.1109 0.021 Uiso 1 1 calc R . .
C13 C 0.05645(16) 0.88196(19) 0.13975(6) 0.0166(3) Uani 1 1 d . . .
H13 H 0.0210 0.9336 0.1742 0.020 Uiso 1 1 calc R . .
N1 N -0.19859(13) 0.53976(17) 0.16511(5) 0.0167(2) Uani 1 1 d . . .
N2 N 0.25592(13) 1.05170(17) 0.01191(5) 0.0172(2) Uani 1 1 d . . .
O1 O 0.30847(14) 0.97493(17) -0.02992(4) 0.0295(3) Uani 1 1 d . . .
O2 O 0.26337(13) 1.22795(15) 0.02168(4) 0.0250(2) Uani 1 1 d . . .
S1 S 0.10537(4) 0.40492(5) 0.211649(14) 0.01849(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 C6 99.93(10) . . ?
N1 C1 C2 100.14(10) . . ?
C6 C1 C2 109.39(11) . . ?
N1 C1 H1 115.1 . . ?
C6 C1 H1 115.1 . . ?
C2 C1 H1 115.1 . . ?
C1 C2 C3 103.32(10) . . ?
C1 C2 H2A 111.1 . . ?
C3 C2 H2A 111.1 . . ?
C1 C2 H2B 111.1 . . ?
C3 C2 H2B 111.1 . . ?
H2A C2 H2B 109.1 . . ?
C4 C3 C2 102.83(11) . . ?
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 C5 100.51(10) . . ?
N1 C4 C3 100.00(10) . . ?
C5 C4 C3 109.33(10) . . ?
N1 C4 H4 115.0 . . ?
C5 C4 H4 115.0 . . ?
C3 C4 H4 115.0 . . ?
C4 C5 C6 103.00(10) . . ?
C4 C5 H5A 111.2 . . ?
C6 C5 H5A 111.2 . . ?
C4 C5 H5B 111.2 . . ?
C6 C5 H5B 111.2 . . ?
H5A C5 H5B 109.1 . . ?
C1 C6 C5 103.00(11) . . ?
C1 C6 H6A 111.2 . . ?
C5 C6 H6A 111.2 . . ?
C1 C6 H6B 111.2 . . ?
C5 C6 H6B 111.2 . . ?
H6A C6 H6B 109.1 . . ?
N1 C7 C8 116.55(11) . . ?
N1 C7 S1 125.22(10) . . ?
C8 C7 S1 118.22(9) . . ?
C9 C8 C13 120.13(11) . . ?
C9 C8 C7 118.36(11) . . ?
C13 C8 C7 121.45(11) . . ?
C10 C9 C8 120.44(12) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C9 C10 C11 118.28(12) . . ?
C9 C10 H10 120.9 . . ?
C11 C10 H10 120.9 . . ?
C10 C11 C12 122.74(12) . . ?
C10 C11 N2 117.95(11) . . ?
C12 C11 N2 119.31(11) . . ?
C13 C12 C11 118.55(12) . . ?
C13 C12 H12 120.7 . . ?
C11 C12 H12 120.7 . . ?
C12 C13 C8 119.85(12) . . ?
C12 C13 H13 120.1 . . ?
C8 C13 H13 120.1 . . ?
C7 N1 C4 131.46(11) . . ?
C7 N1 C1 129.65(11) . . ?
C4 N1 C1 98.55(9) . . ?
O1 N2 O2 123.53(11) . . ?
O1 N2 C11 117.94(11) . . ?
O2 N2 C11 118.53(10) . . ?
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 1.4854(15) . ?
C1 C6 1.5367(18) . ?
C1 C2 1.5389(19) . ?
C1 H1 1.0000 . ?
C2 C3 1.5551(19) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.5378(18) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 N1 1.4850(15) . ?
C4 C5 1.5369(19) . ?
C4 H4 1.0000 . ?
C5 C6 1.559(2) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 N1 1.3119(16) . ?
C7 C8 1.4981(17) . ?
C7 S1 1.6739(13) . ?
C8 C9 1.3954(17) . ?
C8 C13 1.3974(18) . ?
C9 C10 1.3860(18) . ?
C9 H9 0.9500 . ?
C10 C11 1.3830(18) . ?
C10 H10 0.9500 . ?
C11 C12 1.3861(18) . ?
C11 N2 1.4755(16) . ?
C12 C13 1.3904(18) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
N2 O1 1.2260(15) . ?
N2 O2 1.2247(15) . ?
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 32.68(12) . . . . ?
C6 C1 C2 C3 -71.72(13) . . . . ?
C1 C2 C3 C4 1.28(13) . . . . ?
C2 C3 C4 N1 -34.81(12) . . . . ?
C2 C3 C4 C5 70.15(12) . . . . ?
N1 C4 C5 C6 32.43(12) . . . . ?
C3 C4 C5 C6 -72.19(13) . . . . ?
N1 C1 C6 C5 -34.95(12) . . . . ?
C2 C1 C6 C5 69.59(13) . . . . ?
C4 C5 C6 C1 1.56(13) . . . . ?
N1 C7 C8 C9 -101.47(14) . . . . ?
S1 C7 C8 C9 77.21(14) . . . . ?
N1 C7 C8 C13 81.36(15) . . . . ?
S1 C7 C8 C13 -99.96(13) . . . . ?
C13 C8 C9 C10 0.31(19) . . . . ?
C7 C8 C9 C10 -176.90(11) . . . . ?
C8 C9 C10 C11 0.33(19) . . . . ?
C9 C10 C11 C12 -0.49(19) . . . . ?
C9 C10 C11 N2 179.33(11) . . . . ?
C10 C11 C12 C13 0.00(19) . . . . ?
N2 C11 C12 C13 -179.82(11) . . . . ?
C11 C12 C13 C8 0.65(19) . . . . ?
C9 C8 C13 C12 -0.81(18) . . . . ?
C7 C8 C13 C12 176.31(11) . . . . ?
C8 C7 N1 C4 3.3(2) . . . . ?
S1 C7 N1 C4 -175.23(10) . . . . ?
C8 C7 N1 C1 175.18(12) . . . . ?
S1 C7 N1 C1 -3.4(2) . . . . ?
C5 C4 N1 C7 118.17(15) . . . . ?
C3 C4 N1 C7 -129.83(14) . . . . ?
C5 C4 N1 C1 -55.48(11) . . . . ?
C3 C4 N1 C1 56.52(11) . . . . ?
C6 C1 N1 C7 -117.44(14) . . . . ?
C2 C1 N1 C7 130.62(14) . . . . ?
C6 C1 N1 C4 56.38(11) . . . . ?
C2 C1 N1 C4 -55.56(11) . . . . ?
C10 C11 N2 O1 -4.80(17) . . . . ?
C12 C11 N2 O1 175.03(12) . . . . ?
C10 C11 N2 O2 174.53(12) . . . . ?
C12 C11 N2 O2 -5.65(17) . . . . ?
