Diastereoselective Base-Catalyzed Formal [4 + 2] Cycloadditions of N-Sulfonyl Imines and Cyclic Anhydrides.
Laws, Stephen W.; Moore, Lucas C.; Di Maso, Michael J.; Nguyen, Q Nhu N; Tantillo, Dean J.; Shaw, Jared T.; Organic letters 19 (2017) 2466–2469; doi:10.1021/acs.orglett.7b00468

data_1545994
_publ_section_title
;
 Diastereoselective Base-Catalyzed Formal [4 + 2] Cycloadditions of
 N-Sulfonyl Imines and Cyclic Anhydrides.
;
_journal_issue                   10
_journal_name_full               'Organic letters'
_journal_page_first              2466
_journal_page_last               2469
_journal_paper_doi               10.1021/acs.orglett.7b00468
_journal_volume                  19
_journal_year                    2017
_chemical_formula_moiety         'C23 H17 Cl N2 O7 S'
_chemical_formula_sum            'C23 H17 Cl N2 O7 S'
_chemical_formula_weight         500.89
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-07-16
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.16 svn.r3265 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                64.9500(10)
_cell_angle_beta                 76.9800(10)
_cell_angle_gamma                89.3270(10)
_cell_formula_units_Z            2
_cell_length_a                   9.1593(7)
_cell_length_b                   11.0566(8)
_cell_length_c                   12.4050(9)
_cell_measurement_reflns_used    9985
_cell_measurement_temperature    90(2)
_cell_measurement_theta_max      33.08
_cell_measurement_theta_min      2.29
_cell_volume                     1103.85(14)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      90.15
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.929
_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  0.0233
_diffrn_reflns_av_unetI/netI     0.0275
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.929
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            19981
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.929
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.194
_diffrn_reflns_theta_min         1.868
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.317
_exptl_absorpt_correction_T_max  0.7466
_exptl_absorpt_correction_T_min  0.5930
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/4 (Bruker,2014) was used for absorption correction. wR2(int) was 0.0577 before and 0.0338 after correction. The Ratio of minimum to maximum transmission is 0.7943. The \l/2 correction factor is 0.00150.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.507
_exptl_crystal_description       Block
_exptl_crystal_F_000             516
_exptl_crystal_size_max          0.385
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.224
_refine_diff_density_max         0.731
_refine_diff_density_min         -0.417
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     308
_refine_ls_number_reflns         7848
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0451
_refine_ls_R_factor_gt           0.0373
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0570P)^2^+0.3810P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0984
_refine_ls_wR_factor_ref         0.1034
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6727
_reflns_number_total             7848
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b00468_si_001.cif
_cod_data_source_block           mo_mjd011_0m
_cod_depositor_comments
'Adding full bibliography for 1545994--1545995.cif.'
_cod_database_code               1545994
_shelxl_version_number           2014/4
_shelx_estimated_absorpt_t_max   0.932
_shelx_estimated_absorpt_t_min   0.888
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9), C8(H8)
2.b Aromatic/amide H refined with riding coordinates:
 C23(H23), C24(H24), C21(H21), C20(H20), C3(H3), C15(H15), C5(H5), C6(H6),
 C12(H12), C11(H11), C4(H4), C14(H14)
2.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C)
;
_olex2_submission_special_instructions 'No special instructions were received'