A Versatile Enantioselective Synthesis of Barrenazines
Peña-López, Miguel; Martínez, M. Montserrat; Sarandeses, Luis A.; Sestelo, José Pérez; Organic Letters 13 (2011) 4151–; doi:10.1021/ol201592g

data_1502333
_publ_section_title
;
 A Versatile Enantioselective Synthesis of Barrenazines
;
_journal_issue                   15
_journal_name_full               'Organic Letters'
_journal_page_first              4151
_journal_paper_doi               10.1021/ol201592g
_journal_volume                  13
_journal_year                    2011
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C23 H30 N2 O6 S'
_chemical_formula_sum            'C23 H30 N2 O6 S'
_chemical_formula_weight         462.55
_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                 90.569(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   7.5028(4)
_cell_length_b                   5.9354(3)
_cell_length_c                   25.0935(14)
_cell_measurement_reflns_used    2797
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      23.731
_cell_measurement_theta_min      2.435
_cell_volume                     1117.41(10)
_computing_cell_refinement       'SAINT V7.68A (Bruker: Madison, 2009 )'
_computing_data_collection       'Apex2, Bruker Instrument Service v2010, 1-2'
_computing_data_reduction        'SAINT and XPREP Version 2008/2 (Bruker AXS)'
_computing_molecular_graphics    'XP, SHELXTL v. 5.1 (Bruker, 1998)'
_computing_publication_material  'XCIF, 2008/2 (1997-2008 Bruker AXS)'
_computing_structure_refinement  'XL Version 2008/4 (Sheldrick)'
_computing_structure_solution    'XS Version 2008/1 (Sheldrick)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'APEXII area detector'
_diffrn_measurement_method       'phi and omega 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  0.0342
_diffrn_reflns_av_sigmaI/netI    0.0510
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            8595
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.44
_exptl_absorpt_coefficient_mu    0.188
_exptl_absorpt_correction_T_max  0.9815
_exptl_absorpt_correction_T_min  0.9372
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
SADABS Version 2008/1 (Sheldrick, Bruker AXS Inc.)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.375
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             492
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.298
_refine_diff_density_min         -0.541
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.01(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     312
_refine_ls_number_reflns         3874
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0604
_refine_ls_R_factor_gt           0.0504
_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^)+(0.0507P)^2^+0.8536P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1137
_refine_ls_wR_factor_ref         0.1205
_reflns_number_gt                3361
_reflns_number_total             3874
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol201592g_si_002.cif
_cod_data_source_block           1106203_b2_0s
_cod_original_sg_symbol_H-M      P2(1)
_cod_database_code               1502333