(3<i>R</i>,5<i>S</i>,6<i>R</i>,8<i>S</i>,9<i>S</i>)-1-Azonia-9-ethyl-3-hydroxy-5-(6-methoxyquinolin-4-yl)-3-methyl-4-oxatricyclo[6.2.2.0]dodecane trifluoromethanesulfonate: insight into the sterochemistry of the cyclization mechanism
Gema Antequera-García; Bernadette Norberg; Istvan E. Marko; Johan Wouters; Acta Crystallographica Section E 62 (2006) o2864–o2865; doi:10.1107/S1600536806021131

data_2209499
_publ_section_title
;(3<i>R</i>,5<i>S</i>,6<i>R</i>,8<i>S</i>,9<i>S</i>)-1-Azonia-9-ethyl-3-hydroxy-5-(6-methoxyquinolin-4-yl)-3-methyl-4-oxatricyclo[6.2.2.0]dodecane
 trifluoromethanesulfonate: insight into the sterochemistry of the cyclization
 mechanism
;
_journal_coeditor_code           GH2002
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2864
_journal_page_last               o2865
_journal_paper_doi               10.1107/S1600536806021131
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C23 H31 N2 O3 + , C F3 S O3 -'
_chemical_formula_moiety         'C23 H31 N2 O3 + , C F3 S O3 -'
_chemical_formula_sum            'C24 H31 F3 N2 O6 S'
_chemical_formula_weight         532.57
_chemical_name_systematic
;
11<i>S</i>,13<i>R</i>,16<i>R</i>,18<i>S</i>,22<i>S</i>-1-Azonia-9-ethyl-3-
hydroxy-5-(6-methoxy-quinolin-4-yl)-3-methyl-
4-oxatricyclo[6.2.2.0]dodecane trifluoromethanesulfonate
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 101.490(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   11.3120(10)
_cell_length_b                   8.0590(10)
_cell_length_c                   14.0740(10)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      35
_cell_measurement_theta_min      20
_cell_volume                     1257.3(2)
_computing_cell_refinement       CAD4/Mach3
_computing_data_collection       'CAD4/Mach3 (Enraf--Nonius, 2000)'
_computing_data_reduction        'HELENA (Spek, 1997)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  PLATON
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4 diffractometer'
_diffrn_measurement_method       \w/2\q
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0241
_diffrn_reflns_av_sigmaI/netI    0.0238
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2906
_diffrn_reflns_theta_full        75.03
_diffrn_reflns_theta_max         75.03
_diffrn_reflns_theta_min         3.20
_diffrn_standards_decay_%        1.5
_diffrn_standards_interval_count 60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    1.722
_exptl_absorpt_correction_T_max  0.7248
_exptl_absorpt_correction_T_min  0.4801
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   'de Meulenaer & Tompa 1965'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.333
_refine_diff_density_min         -0.342
_refine_ls_abs_structure_details 'not refined (see text)'
_refine_ls_extinction_coef       0.0263(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   0.994
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     333
_refine_ls_number_reflns         2794
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.994
_refine_ls_R_factor_all          0.0473
_refine_ls_R_factor_gt           0.0432
_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/[\s^2^(Fo^2^)+(0.0820P)^2^+0.3280P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1202
_refine_ls_wR_factor_ref         0.1242
_reflns_number_gt                2634
_reflns_number_total             2794
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            gh2002.cif
_cod_data_source_block           I
_cod_original_sg_symbol_Hall     'P 2yb            '
_cod_original_sg_symbol_H-M      'P 21        '
_cod_database_code               2209499