Facile synthesis of chiral ε-sultams via an organocatalytic aza-Friedel-Crafts reaction.
Zhao, Zi-Biao; Shi, Lei; Li, Yaming; Meng, Fan-Jie; Zhou, Yong-Gui; Organic & biomolecular chemistry 17 (2019) 6364–6368; doi:10.1039/c9ob01158g

data_7156909
_publ_section_title
;
 Facile synthesis of chiral \e-sultams via an organocatalytic
 aza-Friedel-Crafts reaction.
;
_journal_issue                   26
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              6364
_journal_page_last               6368
_journal_paper_doi               10.1039/c9ob01158g
_journal_volume                  17
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_sum            'C27 H25 N O5 S'
_chemical_formula_weight         475.54
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_audit_block_doi                 10.5517/ccdc.csd.cc21j7xr
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2019-01-22 deposited with the CCDC.    2019-06-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.0766(8)
_cell_length_b                   9.1009(9)
_cell_length_c                   33.009(4)
_cell_measurement_reflns_used    3987
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      45.704
_cell_measurement_theta_min      4.936
_cell_volume                     2426.3(4)
_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-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0448
_diffrn_reflns_av_unetI/netI     0.0585
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            12503
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.995
_diffrn_reflns_theta_min         2.321
_exptl_absorpt_coefficient_mu    0.171
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6286
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             1000
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.215
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details
; 
 Flack x determined using 986 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.05(6)
_refine_ls_extinction_coef       0.0096(13)
_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   1.076
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     315
_refine_ls_number_reflns         4714
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.092
_refine_ls_R_factor_all          0.0951
_refine_ls_R_factor_gt           0.0503
_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^)+(0.0395P)^2^+0.4147P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0996
_refine_ls_wR_factor_ref         0.1215
_reflns_Friedel_coverage         0.732
_reflns_Friedel_fraction_full    0.991
_reflns_Friedel_fraction_max     0.991
_reflns_number_gt                3063
_reflns_number_total             4714
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ob01158g2.cif
_cod_data_source_block           mo_d8v18550_0m
_cod_depositor_comments          'Adding full bibliography for 7156909.cif.'
_cod_database_code               7156909
_shelx_estimated_absorpt_t_min   0.971
_shelx_estimated_absorpt_t_max   0.980
_shelxl_version_number           2013-4
_shelx_res_checksum              86727