Synthesis of 1H-Isoindoliums by Electrophile-Mediated Cascade Cyclization/Iodination of Propargylamine-based 1,6-Diynes
Wong, Man Kin; Cui, Jian-Fang; Yu, Qiong; O, Wa-Yi; Huang, Liwu; Yang, Bin; Organic & Biomolecular Chemistry  (2022) –; doi:10.1039/D2OB00316C

data_7158629
_publ_section_title
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 Synthesis of 1H-Isoindoliums by Electrophile-Mediated Cascade
 Cyclization/Iodination of Propargylamine-based 1,6-Diynes
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_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_paper_doi               10.1039/D2OB00316C
_journal_year                    2022
_chemical_formula_sum            'C21 H18 Cl F6 I N O P'
_chemical_formula_weight         607.68
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
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2019-06-28 deposited with the CCDC.	2022-04-06 downloaded from the CCDC.
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_cell_angle_alpha                90.00
_cell_angle_beta                 93.944(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.0081(9)
_cell_length_b                   12.9824(11)
_cell_length_c                   17.1316(16)
_cell_measurement_reflns_used    9631
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      26.77
_cell_measurement_theta_min      2.38
_cell_volume                     2220.6(3)
_computing_cell_refinement       'Bruker APEX3'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'D8_VENTURE PHOTOS 100 area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0399
_diffrn_reflns_av_sigmaI/netI    0.0216
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            64193
_diffrn_reflns_theta_full        27.53
_diffrn_reflns_theta_max         27.53
_diffrn_reflns_theta_min         2.29
_exptl_absorpt_coefficient_mu    1.699
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6764
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SAINT
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.818
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       PRISM
_exptl_crystal_F_000             1192
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_refine_diff_density_max         1.010
_refine_diff_density_min         -0.928
_refine_diff_density_rms         0.114
_refine_ls_extinction_coef       0.0006(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     312
_refine_ls_number_reflns         5096
_refine_ls_number_restraints     15
_refine_ls_restrained_S_all      1.009
_refine_ls_R_factor_all          0.0799
_refine_ls_R_factor_gt           0.0622
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0812P)^2^+10.6500P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1739
_refine_ls_wR_factor_ref         0.1851
_reflns_number_gt                3940
_reflns_number_total             5096
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d2ob00316c2.cif
_cod_data_source_block           cjf21
_cod_depositor_comments
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The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Monoclinic' was changed to
'monoclinic' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
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_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               7158629