Synthesis of 3-Hydroxyisoindolin-1-ones Through 1, 4-Dioxane-Mediated Hydroxylhydrative aza-Cyclization of 2-Alkynylbenzamide in Water.
Liu, Renzhi; Yang, Min; Xie, Wenlin; Dong, Wenbi; Zhou, Hongwei; Yadav, Sarita; Potkin, Vladimir Ivanovich; Qiu, Guanyinsheng; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.9b03466

data_4038224
_publ_section_title
;
 Synthesis of 3-Hydroxyisoindolin-1-ones Through 1, 4-Dioxane-Mediated
 Hydroxylhydrative aza-Cyclization of 2-Alkynylbenzamide in Water.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.9b03466
_journal_year                    2020
_chemical_formula_moiety         'C12 H13 Br2 N O4'
_chemical_formula_sum            'C12 H13 Br2 N O4'
_chemical_formula_weight         395.05
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2yc'
_space_group_name_H-M_alt        'I 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-10-08
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 102.001(12)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.5491(15)
_cell_length_b                   8.3129(9)
_cell_length_c                   26.875(4)
_cell_measurement_reflns_used    3381
_cell_measurement_temperature    298.15
_cell_measurement_theta_max      28.9020
_cell_measurement_theta_min      3.8840
_cell_volume                     2742.3(6)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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_temperature      298.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0802
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.870
_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    -22.00  23.00   1.00   29.07    --  -15.89 -99.00 -30.00   45
  2  \w    -40.00 -13.00   1.00   29.07    --  -15.89  87.00 166.00   27
  3  \w     10.00  73.00   1.00   29.07    --   16.05  57.00 150.00   63
  4  \w     52.00  79.00   1.00   29.07    --   16.05 178.00  90.00   27
  5  \w     -1.00  80.00   1.00   29.07    --   16.05  57.00 -60.00   81
  6  \w      4.00  70.00   1.00   29.07    --   16.05  57.00  90.00   66
  7  \w    -13.00  87.00   1.00   29.07    --   16.05  19.00-120.00  100
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0151137000
_diffrn_orient_matrix_UB_12      0.0445292000
_diffrn_orient_matrix_UB_13      -0.0129942000
_diffrn_orient_matrix_UB_21      0.0330445000
_diffrn_orient_matrix_UB_22      0.0260524000
_diffrn_orient_matrix_UB_23      0.0383343000
_diffrn_orient_matrix_UB_31      0.0458163000
_diffrn_orient_matrix_UB_32      -0.0158400000
_diffrn_orient_matrix_UB_33      -0.0189822000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0936
_diffrn_reflns_av_unetI/netI     0.0808
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.870
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            11400
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.870
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.349
_diffrn_reflns_theta_min         2.959
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    5.921
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.04845
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
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    1.914
_exptl_crystal_description       block
_exptl_crystal_F_000             1552
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_refine_diff_density_max         1.634
_refine_diff_density_min         -1.091
_refine_diff_density_rms         0.165
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         3283
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0842
_refine_ls_R_factor_gt           0.0638
_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^)+(0.0955P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1576
_refine_ls_wR_factor_ref         0.1779
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2447
_reflns_number_total             3283
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b03466_si_002.cif
_cod_data_source_block           20190618-1
_cod_database_code               4038224
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H O N Br'
_shelx_estimated_absorpt_t_max   0.589
_shelx_estimated_absorpt_t_min   0.537
_reflns_odcompleteness_completeness 99.78
_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.a Riding coordinates:
 O3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C3(H3A), C6(H6), C4(H4)
2.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C9(H9A,H9B,H9C)
;
_shelx_res_checksum              8216
_shelx_hkl_checksum              82830
_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 5.209
_oxdiff_exptl_absorpt_empirical_full_min 0.465