Enantiomerically pure (1<i>S</i>,5<i>R</i>) and racemic 3-(1-benzothiophen-2-yl)-8-azoniabicyclo[3.2.1]oct-2-ene acetate
Frøstrup, Brian; Peters, Dan; Bond, Andrew D.; Acta Crystallographica Section C 68 (2012) o298–o301; doi:10.1107/S0108270112030569

data_2018560
_publ_section_title
;
 Enantiomerically pure (1<i>S</i>,5<i>R</i>) and racemic
 3-(1-benzothiophen-2-yl)-8-azoniabicyclo[3.2.1]oct-2-ene acetate
;
_journal_coeditor_code           EG3093
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o298
_journal_page_last               o301
_journal_paper_doi               10.1107/S0108270112030569
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C15 H16 N S + , C2 H3 O2 -'
_chemical_formula_moiety         'C15 H16 N S +, C2 H3 O2 -'
_chemical_formula_sum            'C17 H19 N O2 S'
_chemical_formula_weight         301.39
_chemical_name_systematic
;
racemic 3-(1-benzothiophen-2-yl)-8-azoniabicyclo[3.2.1]oct-2-ene acetate
;
_space_group_IT_number           9
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 115.775(11)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.316(3)
_cell_length_b                   14.195(3)
_cell_length_c                   9.020(2)
_cell_measurement_reflns_used    2096
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      24.08
_cell_measurement_theta_min      2.22
_cell_volume                     1535.3(6)
_computing_cell_refinement       'SAINT (Bruker, 2003)'
_computing_data_collection       'APEX2 (Bruker Nonius, 2004)'
_computing_data_reduction        'SAINT (Bruker, 2003)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      180(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.956
_diffrn_measurement_device_type  'Bruker Nonius X8 APEXII CCD area-detector'
_diffrn_measurement_method       'thin-slice \w and \f'
_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  0.0327
_diffrn_reflns_av_sigmaI/netI    0.0509
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6763
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.33
_diffrn_reflns_theta_min         3.81
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.215
_exptl_absorpt_correction_T_max  0.985
_exptl_absorpt_correction_T_min  0.830
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.378
_refine_diff_density_min         -0.223
_refine_ls_abs_structure_details 'Flack (1983), with 731 Friedel pairs'
_refine_ls_abs_structure_Flack   0.08(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2761
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0468
_refine_ls_R_factor_gt           0.0357
_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/[\s^2^(Fo^2^)+(0.0447P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0806
_refine_ls_wR_factor_ref         0.0836
_reflns_number_gt                2318
_reflns_number_total             2761
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            eg3093.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C c'
_cod_database_code               2018560
_cod_database_fobs_code          2018560