#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/15/2211574.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2211574
loop_
_publ_author_name
'Sonar, Vijayakumar N.'
'M. Venkataraj'
'Parkin, Sean'
'Crooks, Peter A.'
_publ_section_title
;
 (Z)-2-(Thiophen-2-ylmethylene)-1-azabicyclo[2.2.2]octan-3-one
;
_journal_coeditor_code           OM2072
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o5869
_journal_page_last               o5870
_journal_paper_doi               10.1107/S1600536806049403
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C12 H13 N O S'
_chemical_formula_moiety         'C12 H13 N O S'
_chemical_formula_sum            'C12 H13 N O S'
_chemical_formula_weight         219.29
_chemical_name_systematic
;
(Z)-2-(Thiophen-2-ylmethylene)-1-azabicyclo[2.2.2]octan-3-one
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 94.6400(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.0171(2)
_cell_length_b                   5.92530(10)
_cell_length_c                   16.1888(2)
_cell_measurement_reflns_used    5645
_cell_measurement_temperature    90.0(2)
_cell_measurement_theta_max      67.96
_cell_measurement_theta_min      2.74
_cell_volume                     1053.34(3)
_computing_cell_refinement       'SAINT (Bruker--Nonius, 2004)'
_computing_data_collection       'APEX2 (Bruker--Nonius, 2004)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'XP in SHELXTL (Sheldrick, 1995)'
_computing_publication_material
;
SHELXL97 and local procedures
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      90.0(2)
_diffrn_detector_area_resol_mean 18
_diffrn_measured_fraction_theta_full .977
_diffrn_measured_fraction_theta_max .977
_diffrn_measurement_device_type  'Bruker--Nonius X8 Proteum'
_diffrn_measurement_method       'ω scans at fixed χ = 55°'
_diffrn_radiation_monochromator  'graded multilayer optics'
_diffrn_radiation_source         'fine-focus rotating anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0312
_diffrn_reflns_av_sigmaI/netI    0.0207
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            11773
_diffrn_reflns_theta_full        67.96
_diffrn_reflns_theta_max         67.96
_diffrn_reflns_theta_min         4.68
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.481
_exptl_absorpt_correction_T_max  0.836
_exptl_absorpt_correction_T_min  0.657
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS in APEX2; Bruker--Nonius, 2004)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.383
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.08
_refine_diff_density_max         .289
_refine_diff_density_min         -.361
_refine_ls_extinction_coef       0.0209(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         1880
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.093
_refine_ls_R_factor_all          0.0370
_refine_ls_R_factor_gt           0.0365
_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)+(0.0559P)²+0.4238P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0891
_refine_ls_wR_factor_ref         0.0907
_reflns_number_gt                1845
_reflns_number_total             1880
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            om2072.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2211574
_cod_database_fobs_code          2211574
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
S S1 -0.00010(3) 0.00858(5) 0.24150(2) 0.01743(17) Uani d . 1
N N1 -0.18759(10) -0.04388(19) 0.35875(7) 0.0162(3) Uani d . 1
O O1 -0.14829(9) 0.29255(17) 0.54515(6) 0.0223(3) Uani d . 1
C C1 0.03102(11) 0.2167(2) 0.31553(8) 0.0156(3) Uani d . 1
C C2 0.10350(12) 0.1220(2) 0.17941(8) 0.0199(3) Uani d . 1
H H2 0.1202 0.0605 0.1273 0.024 Uiso calc R 1
C C3 0.15901(12) 0.3098(2) 0.21300(8) 0.0200(3) Uani d . 1
H H3 0.2186 0.3943 0.1871 0.024 Uiso calc R 1
C C4 0.11756(11) 0.3643(2) 0.29114(8) 0.0181(3) Uani d . 1
H H4 0.1466 0.4900 0.3234 0.022 Uiso calc R 1
C C5 -0.02847(11) 0.2360(2) 0.39141(8) 0.0163(3) Uani d . 1
H H5 0.0051 0.3426 0.4307 0.020 Uiso calc R 1
C C6 -0.12575(11) 0.1206(2) 0.41263(8) 0.0158(3) Uani d . 1
C C7 -0.20399(13) -0.2527(2) 0.40660(8) 0.0207(3) Uani d . 1
H H7A -0.1233 -0.3100 0.4285 0.025 Uiso calc R 1
H H7B -0.2427 -0.3694 0.3694 0.025 Uiso calc R 1
C C8 -0.28423(13) -0.2113(2) 0.47981(9) 0.0220(3) Uani d . 1
H H8A -0.3624 -0.2933 0.4701 0.026 Uiso calc R 1
H H8B -0.2419 -0.2670 0.5321 0.026 Uiso calc R 1
C C9 -0.30797(12) 0.0440(2) 0.48599(8) 0.0184(3) Uani d . 1
H H9 -0.3529 0.0802 0.5356 0.022 Uiso calc R 1
C C10 -0.18689(12) 0.1668(2) 0.48923(8) 0.0166(3) Uani d . 1
C C11 -0.38021(12) 0.1211(2) 0.40535(8) 0.0197(3) Uani d . 1
H H11A -0.3903 0.2871 0.4056 0.024 Uiso calc R 1
H H11B -0.4621 0.0511 0.4010 0.024 Uiso calc R 1
C C12 -0.30920(12) 0.0486(2) 0.33058(8) 0.0181(3) Uani d . 1
H H12A -0.3566 -0.0672 0.2978 0.022 Uiso calc R 1
H H12B -0.2991 0.1806 0.2943 0.022 Uiso calc R 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C .0181 .0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N .0311 .0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O .0492 .0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S .3331 .5567 '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_publ_flag
C2 S1 C1 91.29(6) y
C6 N1 C7 108.69(10) y
C6 N1 C12 107.86(10) ?
C7 N1 C12 108.93(10) ?
C4 C1 C5 124.55(12) y
C4 C1 S1 110.90(10) ?
C5 C1 S1 124.52(10) ?
C3 C2 S1 112.60(10) ?
C3 C2 H2 123.7 ?
S1 C2 H2 123.7 ?
C2 C3 C4 112.09(12) ?
C2 C3 H3 124.0 ?
C4 C3 H3 124.0 ?
C1 C4 C3 113.11(12) ?
C1 C4 H4 123.4 ?
C3 C4 H4 123.4 ?
C6 C5 C1 127.29(12) y
C6 C5 H5 116.4 ?
C1 C5 H5 116.4 ?
C5 C6 N1 122.60(12) y
C5 C6 C10 123.15(12) y
N1 C6 C10 113.97(11) y
N1 C7 C8 111.62(11) ?
N1 C7 H7A 109.3 ?
C8 C7 H7A 109.3 ?
N1 C7 H7B 109.3 ?
C8 C7 H7B 109.3 ?
H7A C7 H7B 108.0 ?
C9 C8 C7 108.35(11) ?
C9 C8 H8A 110.0 ?
C7 C8 H8A 110.0 ?
C9 C8 H8B 110.0 ?
C7 C8 H8B 110.0 ?
H8A C8 H8B 108.4 ?
C10 C9 C8 108.67(11) ?
C10 C9 C11 106.22(11) ?
C8 C9 C11 108.35(11) ?
C10 C9 H9 111.1 ?
C8 C9 H9 111.1 ?
C11 C9 H9 111.1 ?
O1 C10 C6 125.27(12) ?
O1 C10 C9 124.79(12) ?
C6 C10 C9 109.87(11) y
C9 C11 C12 108.65(11) ?
C9 C11 H11A 110.0 ?
C12 C11 H11A 110.0 ?
C9 C11 H11B 110.0 ?
C12 C11 H11B 110.0 ?
H11A C11 H11B 108.3 ?
N1 C12 C11 111.19(11) ?
N1 C12 H12A 109.4 ?
C11 C12 H12A 109.4 ?
N1 C12 H12B 109.4 ?
C11 C12 H12B 109.4 ?
H12A C12 H12B 108.0 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C2 1.7178(13) y
S1 C1 1.7342(13) y
N1 C6 1.4417(16) y
N1 C7 1.4788(17) ?
N1 C12 1.4847(17) ?
O1 C10 1.2219(16) y
C1 C4 1.3751(19) ?
C1 C5 1.4429(18) y
C2 C3 1.361(2) ?
C2 H2 0.9500 ?
C3 C4 1.4166(18) ?
C3 H3 0.9500 ?
C4 H4 0.9500 ?
C5 C6 1.3394(19) y
C5 H5 0.9500 ?
C6 C10 1.4838(17) y
C7 C8 1.5542(19) ?
C7 H7A 0.9900 ?
C7 H7B 0.9900 ?
C8 C9 1.5396(19) ?
C8 H8A 0.9900 ?
C8 H8B 0.9900 ?
C9 C10 1.5169(18) y
C9 C11 1.5422(18) ?
C9 H9 1.0000 ?
C11 C12 1.5539(18) ?
C11 H11A 0.9900 ?
C11 H11B 0.9900 ?
C12 H12A 0.9900 ?
C12 H12B 0.9900 ?
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_publ_flag
C2 S1 C1 C4 0.19(10) ?
C2 S1 C1 C5 178.54(11) ?
C1 S1 C2 C3 -0.22(11) ?
S1 C2 C3 C4 0.19(15) ?
C5 C1 C4 C3 -178.46(12) ?
S1 C1 C4 C3 -0.12(15) ?
C2 C3 C4 C1 -0.05(17) ?
C4 C1 C5 C6 168.73(13) y
S1 C1 C5 C6 -9.4(2) ?
C1 C5 C6 N1 -1.0(2) y
C1 C5 C6 C10 -174.52(12) ?
C7 N1 C6 C5 130.97(13) ?
C12 N1 C6 C5 -111.08(14) ?
C7 N1 C6 C10 -55.00(14) ?
C12 N1 C6 C10 62.96(13) ?
C6 N1 C7 C8 61.81(14) ?
C12 N1 C7 C8 -55.47(14) ?
N1 C7 C8 C9 -7.20(15) ?
C7 C8 C9 C10 -52.17(14) ?
C7 C8 C9 C11 62.83(14) ?
C5 C6 C10 O1 -9.2(2) y
N1 C6 C10 O1 176.83(12) y
C5 C6 C10 C9 167.94(12) ?
N1 C6 C10 C9 -6.06(15) ?
C8 C9 C10 O1 -122.13(14) ?
C11 C9 C10 O1 121.49(14) ?
C8 C9 C10 C6 60.74(13) ?
C11 C9 C10 C6 -55.63(13) ?
C10 C9 C11 C12 62.04(13) ?
C8 C9 C11 C12 -54.55(14) ?
C6 N1 C12 C11 -53.67(14) ?
C7 N1 C12 C11 64.14(14) ?
C9 C11 C12 N1 -7.49(15) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 639368
