Diastereoselective synthesis of cis-1,3-disubstituted isoindolines via a highly site-selective tandem cyclization reaction
Xing, Siyang; Cui, Hong; Qin, Jiajing; Gu, Nan; Zhang, Bowei; Wang, Kui; Wang, Ying; Xia, Li; Wang, Yumeng; Organic Chemistry Frontiers 5 (2018) 1950–; doi:10.1039/C8QO00316E

data_1554308
_publ_section_title
;
 Diastereoselective synthesis of cis-1,3-disubstituted isoindolines via a
 highly site-selective tandem cyclization reaction
;
_journal_issue                   12
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              1950
_journal_paper_doi               10.1039/C8QO00316E
_journal_volume                  5
_journal_year                    2018
_chemical_formula_moiety         'C28 H26 F N O8 S'
_chemical_formula_sum            'C28 H26 F N O8 S'
_chemical_formula_weight         555.56
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2017-04-26
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_audit_update_record
;
2018-01-17 deposited with the CCDC.
2018-05-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   8.2423(2)
_cell_length_b                   18.2962(6)
_cell_length_c                   34.5544(12)
_cell_measurement_reflns_used    3505
_cell_measurement_temperature    117.5(3)
_cell_measurement_theta_max      74.0160
_cell_measurement_theta_min      4.9930
_cell_volume                     5210.9(3)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      117.5(3)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2740
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    153.00 178.00   1.00   10.26    --  107.08 125.00 -30.00   25
  2  \w     99.00 128.00   1.00   10.26    --  107.08 125.00 -30.00   29
  3  \w     98.00 173.00   1.00   10.26    --  107.08 125.00 -90.00   75
  4  \w     35.00 136.00   1.00   10.26    --  107.08 -61.00-180.00  101
  5  \w     84.00 109.00   1.00   10.26    --  107.08 -95.00   0.00   25
  6  \w     25.00  52.00   1.00   10.26    --  107.08 -95.00   0.00   27
  7  \w     22.00  50.00   1.00    2.57    --   41.49 -99.00-180.00   28
  8  \w    -76.00  37.00   1.00    2.57    --  -41.49  19.00-120.00  113
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0172828000
_diffrn_orient_matrix_UB_12      0.0617239000
_diffrn_orient_matrix_UB_13      -0.0300716000
_diffrn_orient_matrix_UB_21      0.0859723000
_diffrn_orient_matrix_UB_22      0.0530880000
_diffrn_orient_matrix_UB_23      0.0278026000
_diffrn_orient_matrix_UB_31      0.1650142000
_diffrn_orient_matrix_UB_32      -0.0214040000
_diffrn_orient_matrix_UB_33      -0.0176721000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0887
_diffrn_reflns_av_unetI/netI     0.0930
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_number            11691
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.079
_diffrn_reflns_theta_max         67.079
_diffrn_reflns_theta_min         4.834
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.628
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.09181
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.416
_exptl_crystal_description       block
_exptl_crystal_F_000             2320
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.428
_refine_diff_density_min         -0.772
_refine_diff_density_rms         0.085
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     355
_refine_ls_number_reflns         4632
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.010
_refine_ls_R_factor_all          0.0828
_refine_ls_R_factor_gt           0.0624
_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^)+(0.0833P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1503
_refine_ls_wR_factor_ref         0.1670
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3418
_reflns_number_total             4632
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8qo00316e2.cif
_cod_data_source_block           a170426b
_cod_database_code               1554308
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C17(H17), C16(H16), C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C14(H14), C2(H2), C23(H23), C27(H27), C6(H6), C11(H11),
 C13(H13), C24(H24), C12(H12), C26(H26)
2.d Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C19(H19A,H19B,H19C), C28(H28A,H28B,H28C)
;
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2017-04-26
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 5.945
_oxdiff_exptl_absorpt_empirical_full_min 0.284