Asymmetric organocatalytic [3 + 2]-annulation strategy for the synthesis of N-fused heteroaromatic compounds
Albrecht, Łukasz; Albrecht, Anna; Ransborg, Lars Krogager; Jørgensen, Karl Anker; Chemical Science 2 (2011) 1273–; doi:10.1039/c1sc00122a

data_1515473
_publ_section_title
;
 Asymmetric organocatalytic [3 + 2]-annulation strategy for the synthesis
 of N-fused heteroaromatic compounds
;
_journal_issue                   7
_journal_name_full               'Chemical Science'
_journal_page_first              1273
_journal_paper_doi               10.1039/c1sc00122a
_journal_volume                  2
_journal_year                    2011
_chemical_absolute_configuration ad
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C18 H21 N3 O2 S1'
_chemical_formula_sum            'C18 H21 N3 O2 S'
_chemical_formula_weight         343.44
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_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_date             2011-02-09T09:56:06-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 91.323(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.7381(4)
_cell_length_b                   7.3170(4)
_cell_length_c                   14.5532(8)
_cell_measurement_reflns_used    9609
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.85
_cell_measurement_theta_min      2.8
_cell_measurement_wavelength     0.71073
_cell_volume                     823.78(8)
_computing_cell_refinement       'Saint+ v7.68A (Bruker-Nonius, 2010)'
_computing_data_collection       'Apex2 (Bruker-Nonius, 2010)'
_computing_data_reduction        'Saint+ v7.68A (Bruker-Nonius, 2010)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 12.00
_diffrn_detector_type            'APEX2 charged-coupled device'
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker X8 APEX-II diffractometer'
_diffrn_measurement_method
;
Narrow slices collected using \f- and \w-scans
;
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0229
_diffrn_reflns_av_unetI/netI     0.014
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            35228
_diffrn_reflns_theta_full        29.85
_diffrn_reflns_theta_max         29.85
_diffrn_reflns_theta_min         2.63
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.213
_exptl_absorpt_correction_T_max  0.942
_exptl_absorpt_correction_T_min  0.881
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS (Sheldrick, 2008)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.385
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.299
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details
'Flack H D (1983), Acta Cryst. A39, 876-881, 1920 Friedel pairs'
_refine_ls_abs_structure_Flack   -0.03(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     223
_refine_ls_number_reflns         4451
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0243
_refine_ls_R_factor_gt           0.0239
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0405P)^2^+0.1656P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0652
_refine_ls_wR_factor_ref         0.0656
_reflns_number_gt                4383
_reflns_number_total             4451
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            c1sc00122a.txt
_cod_data_source_block           11jo0003_0m
_cod_database_code               1515473