#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/28/2202871.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_2202871
loop_
_publ_author_name
'Sonar, Vijayakumar N.'
'Parkin, Sean'
'Crooks, Peter A.'
_publ_section_title
(Z)-2-(Benzo[b]thiophen-3-ylmethylene)-1-azabicyclo[2.2.2]octan-3-one
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1726
_journal_page_last               o1728
_journal_paper_doi               10.1107/S1600536803022797
_journal_volume                  59
_journal_year                    2003
_chemical_formula_iupac          'C16 H15 N O S'
_chemical_formula_moiety         'C16 H15 N O S'
_chemical_formula_sum            'C16 H15 N O S'
_chemical_formula_weight         269.35
_chemical_name_systematic
;
(Z)-(2-Benzo[b]thiophen-3-ylmethylene)-1-azabicyclo[2.2.2]octan-3-one
;
_space_group_IT_number           1
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                102.8959(9)
_cell_angle_beta                 94.7214(9)
_cell_angle_gamma                110.2617(10)
_cell_formula_units_Z            1
_cell_length_a                   6.21440(10)
_cell_length_b                   6.80780(10)
_cell_length_c                   8.4492(2)
_cell_measurement_reflns_used    1439
_cell_measurement_temperature    90.0(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      1.00
_cell_volume                     321.861(11)
_computing_cell_refinement       'SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 1999)'
_computing_data_reduction        DENZO-SMN
_computing_molecular_graphics    'XP in SHELXTL (Sheldrick, 1995)'
_computing_publication_material
;
SHELX97-2 (Sheldrick, 1997) 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 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'ω scans at fixed χ = 55°'
_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  0.0290
_diffrn_reflns_av_sigmaI/netI    0.0316
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            7534
_diffrn_reflns_theta_full        27.46
_diffrn_reflns_theta_max         27.46
_diffrn_reflns_theta_min         2.51
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.242
_exptl_absorpt_correction_T_max  0.9647
_exptl_absorpt_correction_T_min  0.9311
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SCALEPACK; Otwinowski & Minor)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.390
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'irregular block'
_exptl_crystal_F_000             142
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.228
_refine_diff_density_min         -0.181
_refine_ls_abs_structure_details 'Flack (1983), 1389 Friedel pairs '
_refine_ls_abs_structure_Flack   -0.03(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.151
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2858
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.150
_refine_ls_R_factor_all          0.0263
_refine_ls_R_factor_gt           0.0257
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0582P)²+0.0899P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0685
_refine_ls_wR_factor_ref         0.0696
_reflns_number_gt                2811
_reflns_number_total             2858
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            om6181.cif
_cod_data_source_block           I
_cod_original_cell_volume        321.860(10)
_cod_database_code               2202871
_cod_database_fobs_code          2202871
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
loop_
_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
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
S1 -0.45339(5) -0.05949(4) 0.92604(4) 0.01895(9) Uani d . 1 . . S
O1 0.30246(18) -0.22984(16) 0.40849(13) 0.0201(2) Uani d . 1 . . O
C2 -0.2831(2) -0.0260(2) 0.77530(18) 0.0175(3) Uani d . 1 . . C
H2 -0.2842 0.0675 0.7072 0.021 Uiso calc R 1 . . H
C3 -0.1468(2) -0.1465(2) 0.76330(17) 0.0140(3) Uani d . 1 . . C
C4 -0.1761(2) -0.2711(2) 0.88341(16) 0.0136(2) Uani d . 1 . . C
C5 -0.0619(2) -0.4074(2) 0.91554(17) 0.0165(3) Uani d . 1 . . C
H5 0.0470 -0.4338 0.8496 0.020 Uiso calc R 1 . . H
C6 -0.1090(3) -0.5027(2) 1.04343(18) 0.0205(3) Uani d . 1 . . C
H6 -0.0297 -0.5928 1.0662 0.025 Uiso calc R 1 . . H
C7 -0.2724(3) -0.4681(2) 1.14027(19) 0.0217(3) Uani d . 1 . . C
H7 -0.3022 -0.5351 1.2277 0.026 Uiso calc R 1 . . H
C8 -0.3907(2) -0.3375(2) 1.11008(18) 0.0190(3) Uani d . 1 . . C
H8 -0.5032 -0.3157 1.1743 0.023 Uiso calc R 1 . . H
C9 -0.3396(2) -0.2391(2) 0.98267(17) 0.0151(3) Uani d . 1 . . C
C10 0.0068(2) -0.1606(2) 0.64313(16) 0.0141(2) Uani d . 1 . . C
H10 0.0462 -0.2858 0.6253 0.017 Uiso calc R 1 . . H
C11 0.1001(2) -0.0225(2) 0.55452(16) 0.0138(3) Uani d . 1 . . C
N12 0.0745(2) 0.18312(18) 0.56664(15) 0.0146(2) Uani d . 1 . . N
C13 -0.0075(2) 0.1911(2) 0.39986(18) 0.0175(3) Uani d . 1 . . C
H13A -0.0234 0.3325 0.4073 0.021 Uiso calc R 1 . . H
H13B -0.1634 0.0749 0.3561 0.021 Uiso calc R 1 . . H
C14 0.1610(2) 0.1619(2) 0.27835(16) 0.0167(3) Uani d . 1 . . C
H14A 0.0774 0.0346 0.1828 0.020 Uiso calc R 1 . . H
H14B 0.2214 0.2925 0.2372 0.020 Uiso calc R 1 . . H
C15 0.3634(2) 0.1282(2) 0.37065(15) 0.0133(2) Uani d . 1 . . C
H15 0.4737 0.1038 0.2959 0.016 Uiso calc R 1 . . H
C16 0.2599(2) -0.0651(2) 0.44003(16) 0.0140(3) Uani d . 1 . . C
C17 0.4883(2) 0.3298(2) 0.51823(16) 0.0151(3) Uani d . 1 . . C
H17A 0.5534 0.4609 0.4784 0.018 Uiso calc R 1 . . H
H17B 0.6181 0.3112 0.5812 0.018 Uiso calc R 1 . . H
C18 0.3092(2) 0.3571(2) 0.63084(18) 0.0175(3) Uani d . 1 . . C
H18A 0.3649 0.3537 0.7430 0.021 Uiso calc R 1 . . H
H18B 0.2979 0.5004 0.6390 0.021 Uiso calc R 1 . . H
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'
H H 0.0000 0.0000 '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'
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 C9 91.66(7) y
C3 C2 S1 113.61(11) y
C3 C2 H2 123.2 ?
S1 C2 H2 123.2 ?
C2 C3 C4 111.74(12) y
C2 C3 C10 126.39(13) y
C4 C3 C10 121.83(12) ?
C5 C4 C9 118.30(12) ?
C5 C4 C3 129.41(12) ?
C9 C4 C3 112.25(12) ?
C6 C5 C4 119.65(13) ?
C6 C5 H5 120.2 ?
C4 C5 H5 120.2 ?
C5 C6 C7 120.88(14) ?
C5 C6 H6 119.6 ?
C7 C6 H6 119.6 ?
C8 C7 C6 120.90(14) ?
C8 C7 H7 119.6 ?
C6 C7 H7 119.6 ?
C7 C8 C9 117.88(13) ?
C7 C8 H8 121.1 ?
C9 C8 H8 121.1 ?
C8 C9 C4 122.38(13) ?
C8 C9 S1 126.86(11) y
C4 C9 S1 110.73(10) ?
C11 C10 C3 129.26(12) y
C11 C10 H10 115.4 ?
C3 C10 H10 115.4 ?
C10 C11 N12 125.28(12) y
C10 C11 C16 120.76(12) ?
N12 C11 C16 113.80(11) y
C11 N12 C13 108.78(11) ?
C11 N12 C18 107.29(11) ?
C13 N12 C18 108.71(11) ?
N12 C13 C14 112.39(11) y
N12 C13 H13A 109.1 ?
C14 C13 H13A 109.1 ?
N12 C13 H13B 109.1 ?
C14 C13 H13B 109.1 ?
H13A C13 H13B 107.9 ?
C15 C14 C13 108.35(11) ?
C15 C14 H14A 110.0 ?
C13 C14 H14A 110.0 ?
C15 C14 H14B 110.0 ?
C13 C14 H14B 110.0 ?
H14A C14 H14B 108.4 ?
C16 C15 C14 107.76(10) ?
C16 C15 C17 107.37(11) ?
C14 C15 C17 108.28(11) ?
C16 C15 H15 111.1 ?
C14 C15 H15 111.1 ?
C17 C15 H15 111.1 ?
O1 C16 C11 124.87(12) y
O1 C16 C15 125.04(12) y
C11 C16 C15 110.09(10) ?
C15 C17 C18 108.65(11) ?
C15 C17 H17A 110.0 ?
C18 C17 H17A 110.0 ?
C15 C17 H17B 110.0 ?
C18 C17 H17B 110.0 ?
H17A C17 H17B 108.3 ?
N12 C18 C17 111.92(11) y
N12 C18 H18A 109.2 ?
C17 C18 H18A 109.2 ?
N12 C18 H18B 109.2 ?
C17 C18 H18B 109.2 ?
H18A C18 H18B 107.9 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C2 . 1.7259(14) y
S1 C9 . 1.7404(15) y
O1 C16 . 1.2174(16) y
C2 C3 . 1.3631(19) y
C2 H2 . 0.9500 ?
C3 C4 . 1.4460(19) ?
C3 C10 . 1.4598(18) y
C4 C5 . 1.405(2) ?
C4 C9 . 1.4125(17) ?
C5 C6 . 1.381(2) ?
C5 H5 . 0.9500 ?
C6 C7 . 1.404(2) ?
C6 H6 . 0.9500 ?
C7 C8 . 1.386(2) ?
C7 H7 . 0.9500 ?
C8 C9 . 1.392(2) ?
C8 H8 . 0.9500 ?
C10 C11 . 1.3374(18) y
C10 H10 . 0.9500 y
C11 N12 . 1.4447(17) y
C11 C16 . 1.4966(17) y
N12 C13 . 1.4777(19) ?
N12 C18 . 1.4867(18) y
C13 C14 . 1.5556(18) ?
C13 H13A . 0.9900 ?
C13 H13B . 0.9900 ?
C14 C15 . 1.5369(18) y
C14 H14A . 0.9900 ?
C14 H14B . 0.9900 ?
C15 C16 . 1.5196(17) ?
C15 C17 . 1.5426(17) ?
C15 H15 . 1.0000 y
C17 C18 . 1.5545(18) ?
C17 H17A . 0.9900 ?
C17 H17B . 0.9900 ?
C18 H18A . 0.9900 ?
C18 H18B . 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
C9 S1 C2 C3 1.03(11)
S1 C2 C3 C4 -1.04(15)
S1 C2 C3 C10 176.91(11)
C2 C3 C4 C5 -177.23(13)
C10 C3 C4 C5 4.7(2)
C2 C3 C4 C9 0.48(16)
C10 C3 C4 C9 -177.58(11)
C9 C4 C5 C6 -1.04(19)
C3 C4 C5 C6 176.54(13)
C4 C5 C6 C7 1.1(2)
C5 C6 C7 C8 0.0(2)
C6 C7 C8 C9 -1.0(2)
C7 C8 C9 C4 1.0(2)
C7 C8 C9 S1 -176.94(10)
C5 C4 C9 C8 0.00(18)
C3 C4 C9 C8 -177.99(12)
C5 C4 C9 S1 178.26(10)
C3 C4 C9 S1 0.28(13)
C2 S1 C9 C8 177.45(12)
C2 S1 C9 C4 -0.72(10)
C2 C3 C10 C11 21.3(2)
C4 C3 C10 C11 -160.94(14)
C3 C10 C11 N12 3.2(2)
C3 C10 C11 C16 178.37(12)
C10 C11 N12 C13 -127.91(14)
C16 C11 N12 C13 56.65(14)
C10 C11 N12 C18 114.66(15)
C16 C11 N12 C18 -60.78(14)
C11 N12 C13 C14 -58.09(14)
C18 N12 C13 C14 58.43(14)
N12 C13 C14 C15 1.21(15)
C13 C14 C15 C16 56.20(14)
C13 C14 C15 C17 -59.63(14)
C10 C11 C16 O1 6.1(2)
N12 C11 C16 O1 -178.27(13)
C10 C11 C16 C15 -173.27(12)
N12 C11 C16 C15 2.40(15)
C14 C15 C16 O1 121.22(14)
C17 C15 C16 O1 -122.34(14)
C14 C15 C16 C11 -59.45(13)
C17 C15 C16 C11 56.99(13)
C16 C15 C17 C18 -57.50(13)
C14 C15 C17 C18 58.60(14)
C11 N12 C18 C17 58.05(15)
C13 N12 C18 C17 -59.42(14)
C15 C17 C18 N12 0.72(16)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21174630
