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_1554309
_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         '1(C28.75 H27.5 N2 O10 S)'
_chemical_formula_sum            'C28.8 H27.6 N2 O10 S'
_chemical_formula_weight         593.79
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-09-12
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2018-01-17 deposited with the CCDC.
2018-05-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.091(6)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   21.4204(15)
_cell_length_b                   21.5628(12)
_cell_length_c                   14.5587(8)
_cell_measurement_reflns_used    7115
_cell_measurement_temperature    135.00(10)
_cell_measurement_theta_max      28.9210
_cell_measurement_theta_min      3.8350
_cell_volume                     6673.0(7)
_computing_cell_refinement       'CrysAlisPro 1.171.39.29c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.29c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.29c (Rigaku OD, 2017)'
_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      135.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2740
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_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     15.00  40.00   1.00   67.76    --   11.08 -77.00-120.00   25
  2  \w    -13.00  40.00   1.00   67.76    --   11.08  38.00-150.00   53
  3  \w    -16.00  72.00   1.00   67.76    --   11.08  77.00 -60.00   88
  4  \w    -65.00   8.00   1.00   67.76    --   11.08 -77.00-120.00   73
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0082407000
_diffrn_orient_matrix_UB_12      0.0205218000
_diffrn_orient_matrix_UB_13      -0.0260006000
_diffrn_orient_matrix_UB_21      -0.0009902000
_diffrn_orient_matrix_UB_22      0.0253635000
_diffrn_orient_matrix_UB_23      0.0209517000
_diffrn_orient_matrix_UB_31      0.0483964000
_diffrn_orient_matrix_UB_32      0.0040124000
_diffrn_orient_matrix_UB_33      0.0001845000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0315
_diffrn_reflns_av_unetI/netI     0.0413
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            35717
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.008
_diffrn_reflns_theta_max         25.008
_diffrn_reflns_theta_min         3.422
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.149
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87329
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.29c (Rigaku Oxford Diffraction, 2017)
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    1.182
_exptl_crystal_description       block
_exptl_crystal_F_000             2483
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.2
_platon_squeeze_details
;
TITL A170908b  P 21/c       R = 0.18
CELL   21.4204   21.5628   14.5587     90.00     97.09     90.00
SPGR P21/c
C101 0.732 0.629 0.427 !       5.04 eA-3
C102 0.256 0.221 0.162 !       4.14 eA-3
C103 0.760 0.691 0.388 !       4.09 eA-3
C104 0.175 0.185 0.050 !       3.79 eA-3
C105 0.245 0.116 0.354 !       3.75 eA-3
C106 0.229 0.139 0.422 !       3.64 eA-3
C107 0.330 0.125 0.142 !       3.52 eA-3
C108 0.251 0.188 0.387 !       3.52 eA-3
C109 0.313 0.194 0.456 !       3.07 eA-3
C110 0.636 0.570 0.393 !       3.04 eA-3
C111 0.757 0.728 0.150 !       2.84 eA-3
C112 0.163 0.107 0.267 !       2.65 eA-3
C113 0.860 0.578 0.105 !       2.54 eA-3
C114 0.795 0.588 0.200 !       2.45 eA-3
C115 0.252 0.119 0.137 !       2.23 eA-3
C116 0.766 0.523 0.231 !       2.05 eA-3
C117 0.834 0.634 0.135 !       2.02 eA-3
Q118 0.299 0.855 0.185 !       1.47 eA-3
C119 0.333 0.102 0.265 !       1.41 eA-3
Q120 0.251 0.883 0.109 !       1.37 eA-3
Q121 0.190 0.462 0.051 !       1.34 eA-3
C122 0.274 0.249 0.454 !       1.29 eA-3
C123 0.667 0.610 0.304 !       1.26 eA-3
C124 0.298 0.100 0.205 !       1.26 eA-3
C125 0.725 0.523 0.229 !       1.25 eA-3
Q126 0.826 0.857 0.378 !       1.24 eA-3
C127 0.352 0.116 0.089 !       1.24 eA-3
Q128 0.369 0.558 0.193 !       1.21 eA-3
C129 0.267 0.490 0.715 !       1.21 eA-3
C130 0.733 0.510 0.285 !       1.21 eA-3
Q131 0.323 0.800 0.145 !       1.21 eA-3
Q132 0.703 0.278 0.428 !       1.20 eA-3
C133 0.773 0.701 0.480 !       1.19 eA-3
Q134 0.197 0.856 0.330 !       1.12 eA-3
C135 0.679 0.575 0.350 !       1.06 eA-3
Q136 0.306 0.462 0.457 !       1.05 eA-3
C137 0.679 0.925 0.822 !       1.05 eA-3
C138 0.299 0.317 0.015 !       1.04 eA-3
Q139 0.307 0.549 0.142 !       1.04 eA-3
Q140 0.759 0.390 0.124 !       1.02 eA-3
Q141 0.241 0.610 0.876 !       1.02 eA-3
C142 0.666 0.630 0.258 !       1.01 eA-3
Q143 0.803 0.285 0.059 !       0.98 eA-3
C144 0.304 0.069 0.238 !       0.98 eA-3
Q145 0.158 0.420 0.111 !       0.96 eA-3
C146 0.310 0.032 0.235 !       0.94 eA-3
C147 0.213 0.073 0.392 !       0.93 eA-3
C148 0.266 0.242 0.387 !       0.92 eA-3
Q149 0.178 0.802 0.356 !       0.91 eA-3
Q150 0.256 0.621 0.903 !       0.90 eA-3
C151 0.755 0.536 0.299 !       0.89 eA-3
C152 0.306 0.152 0.139 !       0.89 eA-3
C153 0.669 0.587 0.436 !       0.89 eA-3
Q154 0.421 0.413 0.266 !       0.88 eA-3
C155 0.783 0.505 0.311 !       0.87 eA-3
C156 0.252 0.242 0.493 !       0.85 eA-3
Q157 0.674 0.866 0.121 !       0.84 eA-3
Q158 0.836 0.172 0.377 !       0.83 eA-3
C159 0.235 0.236 0.017 !       0.82 eA-3
Q160 0.393 0.635 0.109 !       0.80 eA-3
C161 0.248 0.051 0.344 !       0.79 eA-3
Q162 0.139 0.569 0.331 !       0.78 eA-3
C163 0.705 0.507 0.333 !       0.77 eA-3
C164 0.790 0.659 0.484 !       0.75 eA-3
C165 0.180 0.344 0.485 !       0.75 eA-3
C166 0.693 0.502 0.185 !       0.74 eA-3
Q167 0.698 0.891 0.224 !       0.74 eA-3
C168 0.587 0.554 0.426 !       0.74 eA-3
Q169 0.148 0.323 0.183 !       0.73 eA-3
Q170 0.901 0.062-0.007 !       0.73 eA-3
Q171 0.650 0.662 0.373 !       0.72 eA-3
C172 0.311 0.157 0.412 !       0.71 eA-3
C173 0.110 0.042 0.377 !       0.69 eA-3
Q174 0.392 0.366 0.247 !       0.69 eA-3
Q175 0.782 0.773 0.423 !       0.68 eA-3
C176 0.274 0.014 0.379 !       0.67 eA-3
Q177 0.349 0.643 0.050 !       0.66 eA-3
C178 0.818 0.507 0.127 !       0.66 eA-3
Q179 0.658 0.843 0.265 !       0.66 eA-3
C180 0.172 0.126 0.438 !       0.65 eA-3
Q181 0.851 0.856 0.247 !       0.65 eA-3
C182 0.696 0.756 0.076 !       0.64 eA-3
C183 0.194 0.258 0.049 !       0.64 eA-3
C184 0.792 0.689 0.342 !       0.63 eA-3
C185 0.726 0.782 0.019 !       0.63 eA-3
Q186 0.188 0.065 0.438 !       0.63 eA-3
Q187 0.281 0.869 0.374 !       0.62 eA-3
Q188 0.539 0.820 0.343 !       0.62 eA-3
Q189 0.171 0.449 0.204 !       0.62 eA-3
Q190 0.866 0.540 0.234 !       0.62 eA-3
Q191 0.898 0.561 0.142 !       0.62 eA-3
C192 0.765 0.781 0.048 !       0.61 eA-3
C193 0.157 0.031 0.239 !       0.61 eA-3
C194 0.272 0.181 0.218 !       0.61 eA-3
Q195 0.391 0.051 0.455 !       0.61 eA-3
Q196 0.852 0.775 0.021 !       0.60 eA-3
C197 0.695 0.798 0.026 !       0.60 eA-3
C198 0.101 0.081 0.420 !       0.60 eA-3
C199 0.812 0.740 0.388 !       0.60 eA-3
;
_refine_diff_density_max         1.097
_refine_diff_density_min         -0.662
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     765
_refine_ls_number_reflns         11718
_refine_ls_number_restraints     144
_refine_ls_restrained_S_all      1.101
_refine_ls_R_factor_all          0.1508
_refine_ls_R_factor_gt           0.0971
_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^)+(0.1399P)^2^+13.3247P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2658
_refine_ls_wR_factor_ref         0.3200
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6075
_reflns_number_total             11718
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8qo00316e2.cif
_cod_data_source_block           a170908b_sq
_cod_original_formula_sum        'C28.80 H27.60 N2 O10 S'
_cod_database_code               1554309
_shelx_shelxl_version_number     2014/7
_reflns_odcompleteness_completeness 99.69
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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, All O(H) groups
2. Uiso/Uaniso restraints and constraints
C1 \\sim C2 \\sim C3 \\sim C4 \\sim C5 \\sim C6: within 2A with sigma of 0.001
and sigma for terminal atoms of 0.002
Uanis(C4) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.002
Uanis(O7) \\sim Ueq, Uanis(O8) \\sim Ueq: with sigma of 0.005 and sigma for
terminal atoms of 0.002
Uanis(C12) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.002
Uanis(O23) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.002
Uanis(C13) \\sim Ueq, Uanis(C7) \\sim Ueq, Uanis(C5) \\sim Ueq, Uanis(C6) \\sim
Ueq, Uanis(C36) \\sim Ueq, Uanis(C34) \\sim Ueq, Uanis(C35) \\sim Ueq,
Uanis(C33) \\sim Ueq, Uanis(C32) \\sim Ueq, Uanis(C40) \\sim Ueq, Uanis(C42)
\\sim Ueq, Uanis(O13) \\sim Ueq, Uanis(O14) \\sim Ueq: with sigma of 0.005 and
sigma for terminal atoms of 0.002
3. Others
 Fixed Sof: H8(0.25) C13(0.75) H13A(0.75) H13B(0.75) H13C(0.75) H19A(0.15)
 C42(0.85) H42A(0.85) H42B(0.85) H42C(0.85)
4.a Ternary CH refined with riding coordinates:
 C8(H8A), C9(H9), C21(H21), C37(H37), C38(H38), C50(H50)
4.b Secondary CH2 refined with riding coordinates:
 C20(H20A,H20B), C22(H22A,H22B), C49(H49A,H49B), C51(H51A,H51B)
4.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C16(H16), C17(H17), C18(H18), C19(H19),
 C25(H25), C26(H26), C28(H28), C29(H29), C31(H31), C32(H32), C34(H34), C35(H35),
  C44(H44), C45(H45), C46(H46), C47(H47), C54(H54), C55(H55), C57(H57), C58(H58)
4.d Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C11(H11A,H11B,H11C), C13(H13A,H13B,H13C), C36(H36A,H36B,
 H36C), C40(H40A,H40B,H40C), C42(H42A,H42B,H42C)
4.e Idealised tetrahedral OH refined as rotating group:
 O8(H8), O19(H19A)
;
_platon_squeeze_void_probe_radius 1.20
_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 1.183
_oxdiff_exptl_absorpt_empirical_full_min 0.787