Approach to Chiral 1-Substituted Isoquinolone and 3-Substituted Isoindolin-1-one by Addition-Cyclization Process.
Zhou, Wen; Zhang, Yan-Xue; Nie, Xiao-Di; Si, Chang-Mei; Sun, Xun; Wei, Bang-Guo; The Journal of organic chemistry 83 (2018) 9879–9889; doi:10.1021/acs.joc.8b01282

data_4035114
_publ_section_title
;
 Approach to Chiral 1-Substituted Isoquinolone and 3-Substituted
 Isoindolin-1-one by Addition-Cyclization Process.
;
_journal_issue                   17
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              9879
_journal_page_last               9889
_journal_paper_doi               10.1021/acs.joc.8b01282
_journal_volume                  83
_journal_year                    2018
_chemical_absolute_configuration S,S,S,S
_chemical_formula_moiety         'C26 H25 N O4 S'
_chemical_formula_sum            'C26 H25 N O4 S'
_chemical_formula_weight         447.53
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2018-06-21
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 108.675(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   10.9996(5)
_cell_length_b                   44.458(2)
_cell_length_c                   11.2795(5)
_cell_measurement_reflns_used    9200
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.94
_cell_measurement_theta_min      2.39
_cell_volume                     5225.5(4)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 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    'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0523
_diffrn_reflns_av_unetI/netI     0.0351
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       54
_diffrn_reflns_limit_k_min       -54
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            122275
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_min         1.960
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.153
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6773
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1577 before and 0.0660 after correction.
The Ratio of minimum to maximum transmission is 0.9084.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.138
_exptl_crystal_description       block
_exptl_crystal_F_000             1888
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.328
_refine_diff_density_min         -0.336
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details
;
 Flack x determined using 6891 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.012(16)
_refine_ls_extinction_coef       0.0090(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1154
_refine_ls_number_reflns         20499
_refine_ls_number_restraints     53
_refine_ls_restrained_S_all      1.085
_refine_ls_R_factor_all          0.0575
_refine_ls_R_factor_gt           0.0491
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0887P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1299
_refine_ls_wR_factor_ref         0.1369
_reflns_Friedel_coverage         0.973
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                17249
_reflns_number_total             20499
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b01282_si_002.cif
_cod_data_source_block           mo_d8v18051_0m_sq
_cod_database_code               4035114
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.985
_shelx_estimated_absorpt_t_min   0.970
_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. Rigid bond restraints
 C75, C78, C28, C33, C97, C98, C101, C102, C101, C103
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
 C71, C72, C72, C73, S4, C101, C96, C97, S2, O8, C73, C74, C101, C104
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
3. Uiso/Uaniso restraints and constraints
Uanis(C72) \\sim Ueq, Uanis(C97) \\sim Ueq, Uanis(C104) \\sim Ueq, Uanis(C101)
\\sim Ueq, Uanis(C102) \\sim Ueq, Uanis(C103) \\sim Ueq: with sigma of 0.001
and sigma for terminal atoms of 0.002
4.a Ternary CH refined with riding coordinates:
 C10(H10), C36(H36), C62(H62), C88(H88)
4.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C8(H8A,H8B), C27(H27A,H27B), C34(H34A,H34B), C53(H53A,H53B),
 C60(H60A,H60B), C79(H79A,H79B), C86(H86A,H86B)
4.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C7(H7), C12(H12), C13(H13), C15(H15), C16(H16), C18(H18), C19(H19),
 C20(H20), C21(H21), C22(H22), C30(H30), C33(H33), C38(H38), C39(H39), C41(H41),
  C42(H42), C44(H44), C45(H45), C46(H46), C47(H47), C48(H48), C56(H56),
 C59(H59), C64(H64), C65(H65), C67(H67), C68(H68), C70(H70), C71(H71), C72(H72),
  C73(H73), C74(H74), C82(H82), C85(H85), C90(H90), C91(H91), C93(H93),
 C94(H94), C100(H100), C99(H99), C98(H98), C97(H97), C96(H96)
4.d Fitted hexagon refined as free rotating group:
 C95(C100,C99,C98,C97,C96)
4.e Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C25(H25A,H25B,H25C), C26(H26A,H26B,H26C), C50(H50A,H50B,
 H50C), C51(H51A,H51B,H51C), C52(H52A,H52B,H52C), C76(H76A,H76B,H76C), C77(H77A,
 H77B,H77C), C78(H78A,H78B,H78C), C102(H10A,H10B,H10C), C103(H10D,H10E,H10F),
 C104(H10G,H10H,H10I)
;
_shelx_res_checksum              63807
_shelx_hkl_checksum              96557
_shelx_fab_checksum              56594
_platon_squeeze_void_probe_radius 1.20
_olex2_submission_special_instructions 'No special instructions were received'