Dual Catalysis in Enantioselective Oxidopyrylium-Based [5 + 2] Cycloadditions
Noah Z. Burns; Michael R. Witten; Eric N. Jacobsen; Journal of the American Chemical Society 133 (2011) 14578–14581; doi:10.1021/ja206997e

data_4106787
_publ_section_title
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 Dual Catalysis in Enantioselective Oxidopyrylium-Based [5 + 2]
 Cycloadditions
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_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              14578
_journal_page_last               14581
_journal_paper_doi               10.1021/ja206997e
_journal_volume                  133
_journal_year                    2011
_chemical_absolute_configuration rm
_chemical_formula_sum            'C25 H27 N3 S'
_chemical_formula_weight         401.56
_chemical_name_systematic
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 ? 
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_space_group_IT_number           144
_symmetry_cell_setting           trigonal
_symmetry_space_group_name_Hall  'P 31'
_symmetry_space_group_name_H-M   'P 31'
_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                 90.00
_cell_angle_gamma                120.00
_cell_formula_units_Z            3
_cell_length_a                   11.4229(4)
_cell_length_b                   11.4229(4)
_cell_length_c                   14.1312(5)
_cell_measurement_temperature    100(2)
_cell_volume                     1596.84(10)
_computing_cell_refinement       'SAINT 7.46A (Bruker-AXS, 2009)'
_computing_data_collection       'APEX2 v2009.3.0 (Bruker-AXS, 2009)'
_computing_data_reduction        'SAINT 7.46A (Bruker-AXS, 2009)'
_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      100(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  '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  0.0479
_diffrn_reflns_av_sigmaI/netI    0.0203
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            32886
_diffrn_reflns_theta_full        66.57
_diffrn_reflns_theta_max         66.57
_diffrn_reflns_theta_min         4.47
_exptl_absorpt_coefficient_mu    1.457
_exptl_absorpt_correction_T_max  0.8446
_exptl_absorpt_correction_T_min  0.7032
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.253
_exptl_crystal_description       needle
_exptl_crystal_F_000             642
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.406
_refine_diff_density_min         -0.330
_refine_diff_density_rms         0.056
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -10(10)
_refine_ls_extinction_coef       0.0082(5)
_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   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     249
_refine_ls_number_reflns         3653
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.0902
_refine_ls_R_factor_gt           0.0898
_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^)+(0.0248P)^2^+3.3770P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1773
_refine_ls_wR_factor_ref         0.1776
_reflns_number_gt                3637
_reflns_number_total             3653
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja206997e_si_002.cif
_cod_data_source_block           2,6-ph2-cat
_cod_depositor_comments
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The following automatic conversions were performed:

'_symmetry_cell_setting' tag value 'trigona' was replaced with
'trigonal' value as specified in the replacement file
'/home/robertas/cod-tools/perl-scripts/inputs/replacement_values.lst'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
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_cod_database_code               4106787