Enantioselective synthesis of a highly potent selective serotonin reuptake inhibitor. An application of imidazolidinone catalysis to the alkylation of indoles with an alpha,beta-disubstituted alpha,beta-unsaturated aldehyde.
King, H. Dalton; Meng, Zhaoxing; Denhart, Derek; Mattson, Ronald; Kimura, Roy; Wu, Dedong; Gao, Qi; Macor, John E.; Organic letters 7 (2005) 3437–3440; doi:10.1021/ol051000c

data_1506609
_publ_section_title
;
 Enantioselective synthesis of a highly potent selective serotonin
 reuptake inhibitor. An application of imidazolidinone catalysis to the
 alkylation of indoles with an alpha,beta-disubstituted
 alpha,beta-unsaturated aldehyde.
;
_journal_issue                   16
_journal_name_full               'Organic letters'
_journal_page_first              3437
_journal_page_last               3440
_journal_paper_doi               10.1021/ol051000c
_journal_volume                  7
_journal_year                    2005
_chemical_formula_sum            'C14 H14 I N O'
_chemical_formula_weight         339.16
_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                 103.787(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   7.1606(1)
_cell_length_b                   8.5952(1)
_cell_length_c                   11.1713(1)
_cell_measurement_reflns_used    3415
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      67.8
_cell_measurement_theta_min      4.1
_cell_volume                     667.748(14)
_computing_cell_refinement       'Bruker SAINTPLUS'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINTPLUS'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.942
_diffrn_measured_fraction_theta_max 0.942
_diffrn_measurement_device_type  'SMART 2K CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0702
_diffrn_reflns_av_sigmaI/netI    0.0517
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            3545
_diffrn_reflns_theta_full        67.68
_diffrn_reflns_theta_max         67.68
_diffrn_reflns_theta_min         4.07
_exptl_absorpt_coefficient_mu    18.703
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.364
_exptl_absorpt_correction_type   SADABS
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.687
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.195
_refine_diff_density_min         -0.862
_refine_diff_density_rms         0.204
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.011(17)
_refine_ls_extinction_coef       0.010(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         1873
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0795
_refine_ls_R_factor_gt           0.0792
_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^)+(0.1870P)^2^+0.2100P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2106
_refine_ls_wR_factor_ref         0.2115
_reflns_number_gt                1835
_reflns_number_total             1873
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol051000csi20050502_052116.cif
_cod_data_source_block           10b
_cod_depositor_comments
;
The following automatic conversions were performed:
'_atom_site_symetry_multiplicity' tag replaced with
'_atom_site_symmetry_multiplicity'.

Automatic conversion script
Id: cif_correct_tags 1440 2010-10-19 06:21:57Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P2(1)
_cod_original_formula_sum        'C14 H14 I1 N1 O1'
_cod_database_code               1506609