Synthesis of tricyclic 3-hydroxyisoindolin-1-ones via triethylamine-catalyzed domino reactions of electron-deficient alkynes with phthalimidomalonate derivatives
Zhang, Li; Zhang, Beichen; Jiang, Teng; Lu, Tao; Zhou, Qingfa; Organic Chemistry Frontiers 4 (2017) 119–; doi:10.1039/C6QO00544F

data_1553566
_publ_section_title
;
 Synthesis of tricyclic 3-hydroxyisoindolin-1-ones via
 triethylamine-catalyzed domino reactions of electron-deficient alkynes
 with phthalimidomalonate derivatives
;
_journal_issue                   1
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              119
_journal_paper_doi               10.1039/C6QO00544F
_journal_volume                  4
_journal_year                    2017
_chemical_formula_sum            'C20 H21 N O8'
_chemical_formula_weight         403.38
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2016-07-15 deposited with the CCDC.
2016-10-24 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 107.19(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.1010(16)
_cell_length_b                   19.041(4)
_cell_length_c                   13.693(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      13
_cell_measurement_theta_min      9
_cell_volume                     2017.8(8)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Nonius CAD4'
_diffrn_measurement_method       \w/2\q
_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  0.1349
_diffrn_reflns_av_sigmaI/netI    0.1554
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7831
_diffrn_reflns_theta_full        25.40
_diffrn_reflns_theta_max         25.40
_diffrn_reflns_theta_min         1.89
_diffrn_standards_decay_%        1
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  2h
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_T_max  0.9897
_exptl_absorpt_correction_T_min  0.9696
_exptl_absorpt_correction_type   psi-scan
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.349
_refine_diff_density_min         -0.351
_refine_diff_density_rms         0.083
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         3714
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.1304
_refine_ls_R_factor_gt           0.0679
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0800P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1552
_refine_ls_wR_factor_ref         0.1807
_reflns_number_gt                1841
_reflns_number_total             3714
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6qo00544f2.cif
_cod_data_source_block           x
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Monoclinic' was changed to
'monoclinic' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/RSC/depositions/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 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_cell_volume        2017.8(7)
_cod_original_sg_symbol_H-M      P21/C
_cod_database_code               1553566