Tin Powder-Promoted Cascade Condensation/Allylation/Lactamization: Synthesis of Isoindolinones and Pyrazoloisoindol-8-ones.
Wang, Xiaoping; Huang, Danfeng; Wang, Ke-Hu; Su, Yingpeng; Hu, Yulai; The Journal of organic chemistry 84 (2019) 6946–6961; doi:10.1021/acs.joc.9b00733

data_4034643
_publ_section_title
;
 Tin Powder-Promoted Cascade Condensation/Allylation/Lactamization:
 Synthesis of Isoindolinones and Pyrazoloisoindol-8-ones.
;
_journal_issue                   11
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              6946
_journal_page_last               6961
_journal_paper_doi               10.1021/acs.joc.9b00733
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C18 H15 I N2 O2'
_chemical_formula_sum            'C18 H15 I N2 O2'
_chemical_formula_weight         418.22
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2018-12-14
_audit_creation_method
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Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                64.977(13)
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_cell_angle_gamma                84.893(11)
_cell_formula_units_Z            2
_cell_length_a                   6.5779(9)
_cell_length_b                   11.3665(14)
_cell_length_c                   12.6177(18)
_cell_measurement_reflns_used    1380
_cell_measurement_temperature    292.87(10)
_cell_measurement_theta_max      24.4890
_cell_measurement_theta_min      3.5950
_cell_volume                     838.3(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
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_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
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_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      292.87(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega  -11.00   17.50   1.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.4273  -99.0000  -60.0000 19

  2 omega  -20.00   13.00   1.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.4273  -99.0000   90.0000 22

  3 omega   74.00  101.00   1.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  178.0000  150.0000 18

  4 omega   -1.00   92.00   1.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867   57.0000  -60.0000 62

  5 omega  -34.00   86.00   1.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  -19.0000  -30.0000 80

  6 omega  -47.00   46.00   1.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  -57.0000  150.0000 62
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0860841000
_diffrn_orient_matrix_UB_12      -0.0421597000
_diffrn_orient_matrix_UB_13      0.0150574000
_diffrn_orient_matrix_UB_21      0.0232129000
_diffrn_orient_matrix_UB_22      0.0033505000
_diffrn_orient_matrix_UB_23      -0.0585177000
_diffrn_orient_matrix_UB_31      0.0643492000
_diffrn_orient_matrix_UB_32      0.0543527000
_diffrn_orient_matrix_UB_33      -0.0178618000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0334
_diffrn_reflns_av_unetI/netI     0.0592
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5524
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.022
_diffrn_reflns_theta_min         3.479
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.921
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74628
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.657
_exptl_crystal_description       block
_exptl_crystal_F_000             412
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_refine_diff_density_max         1.125
_refine_diff_density_min         -1.276
_refine_diff_density_rms         0.125
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3285
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.0924
_refine_ls_R_factor_gt           0.0593
_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^)+(0.0577P)^2^+1.4305P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1363
_refine_ls_wR_factor_ref         0.1671
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2095
_reflns_number_total             3285
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b00733_si_002.cif
_cod_data_source_block           wangxp_1212
_cod_database_code               4034643
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 99.77
_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
2.a Ternary CH refined with riding coordinates:
 C8(H8), C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C18(H18A,H18B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C14(H14), C15(H15), C16(H16), C17(H17)
;
_shelx_res_checksum              26668
_shelx_hkl_checksum              15567
_olex2_date_sample_data_collection 2018-12-14
_olex2_submission_special_instructions 'No special instructions were received'