Direct and highly enantioselective iso-Pictet-Spengler reactions with α-ketoamides: access to underexplored indole core structures.
Schönherr, Heike; Leighton, James L.; Organic letters 14 (2012) 2610–2613; doi:10.1021/ol300922b

data_1507712
_publ_section_title
;
 Direct and highly enantioselective iso-Pictet-Spengler reactions with
 \a-ketoamides: access to underexplored indole core structures.
;
_journal_issue                   10
_journal_name_full               'Organic letters'
_journal_page_first              2610
_journal_page_last               2613
_journal_paper_doi               10.1021/ol300922b
_journal_volume                  14
_journal_year                    2012
_chemical_absolute_configuration ad
_chemical_formula_sum            'C16 H16 N2 O S2'
_chemical_formula_weight         316.43
_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                101.135(2)
_cell_angle_beta                 94.640(2)
_cell_angle_gamma                90.106(2)
_cell_formula_units_Z            4
_cell_length_a                   8.3985(11)
_cell_length_b                   11.9291(15)
_cell_length_c                   15.318(2)
_cell_measurement_reflns_used    9947
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      30.49
_cell_measurement_theta_min      2.41
_cell_volume                     1500.6(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_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  0.0247
_diffrn_reflns_av_sigmaI/netI    0.0673
_diffrn_reflns_limit_h_max       12
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_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            24385
_diffrn_reflns_theta_full        30.58
_diffrn_reflns_theta_max         30.58
_diffrn_reflns_theta_min         1.36
_exptl_absorpt_coefficient_mu    0.354
_exptl_absorpt_correction_T_max  0.9554
_exptl_absorpt_correction_T_min  0.9042
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.347
_refine_diff_density_min         -0.315
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.04(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     762
_refine_ls_number_reflns         17751
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0751
_refine_ls_R_factor_gt           0.0516
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0515P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1048
_refine_ls_wR_factor_ref         0.1173
_reflns_number_gt                13411
_reflns_number_total             17751
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol300922b_si_002.cif
_cod_data_source_block           hi1s10
_cod_depositor_comments
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The following automatic conversions were performed:

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

'_exptl_absorpt_correction_type' value 'EMPIRICAL'
changed to 'empirical' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from
2010-06-29.

'_refine_ls_hydrogen_treatment' value 'CONSTR' changed
to 'constr' 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 

 Adding full bibliography for 1507712--1507713.cif.
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_cod_original_sg_symbol_H-M      P1
_cod_database_code               1507712