Memory of Chirality Approach to the Enantiodivergent Synthesis of Chiral Benzo[d]sultams
Foschi, Francesca; Tagliabue, Aaron; Mihali, Voichita; Pilati, Tullio; Pecnikaj, Ilir; Penso, Michele; Organic Letters 15 (2013) 3686–; doi:10.1021/ol401557v

data_1512189
_publ_section_title
;
 Memory of Chirality Approach to the Enantiodivergent Synthesis of Chiral
 Benzo[d]sultams
;
_journal_issue                   14
_journal_name_full               'Organic Letters'
_journal_page_first              3686
_journal_paper_doi               10.1021/ol401557v
_journal_volume                  15
_journal_year                    2013
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C18 H13 F4 N O4 S'
_chemical_formula_sum            'C18 H13 F4 N O4 S'
_chemical_formula_weight         415.35
_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                 106.620(12)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.8290(12)
_cell_length_b                   19.271(2)
_cell_length_c                   10.0453(12)
_cell_measurement_reflns_used    9975
_cell_measurement_temperature    103(2)
_cell_measurement_theta_max      29.56
_cell_measurement_theta_min      2.12
_cell_volume                     1823.2(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics
;
ORTEP-3 (Farrugia, L.J. (1997) Jour. Appl. Cryst. 30, 565)
Mercury (Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., 
Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). 
J. Appl. Cryst. 39, 453-457
;
_computing_publication_material  SHELXTL
_computing_structure_refinement
'SHELXL (Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122)'
_computing_structure_solution
;
SIR2002 (Burla, M. C., Camalli, M., Carrozzini, B., Cascarano, G. L., 
Giacovazzo, C., Polidori, G. & Spagna, R. (2003). 
J. Appl. Cryst. 36, 1103.)
;
_diffrn_ambient_temperature      103(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.811
_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  0.0594
_diffrn_reflns_av_sigmaI/netI    0.0565
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            26510
_diffrn_reflns_theta_full        28.00
_diffrn_reflns_theta_max         32.92
_diffrn_reflns_theta_min         2.11
_diffrn_standards_decay_%        0.00
_exptl_absorpt_coefficient_mu    0.242
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.513
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.716
_refine_diff_density_min         -0.484
_refine_diff_density_rms         0.105
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.960
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     609
_refine_ls_number_reflns         8567
_refine_ls_number_restraints     158
_refine_ls_restrained_S_all      0.955
_refine_ls_R_factor_all          0.0479
_refine_ls_R_factor_gt           0.0364
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0381P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0704
_refine_ls_wR_factor_ref         0.0735
_reflns_number_gt                7132
_reflns_number_total             8567
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            ol401557v_si_003.cif
_cod_data_source_block           pe04
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               1512189