Regioselective 5-exo-dig oxy-cyclization of 2-alkynylbenzamide for the synthesis of isobenzofuran-1-imines and isobenzofuran.
Wang, Rui-Xiang; Yuan, Si-Tian; Liu, Jin-Biao; Wu, Jie; Qiu, Guanyinsheng; Organic & biomolecular chemistry 16 (2018) 4501–4508; doi:10.1039/c8ob00779a

data_7156270
_publ_section_title
;
 Regioselective 5-exo-dig oxy-cyclization of 2-alkynylbenzamide for the
 synthesis of isobenzofuran-1-imines and isobenzofuran.
;
_journal_issue                   24
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              4501
_journal_page_last               4508
_journal_paper_doi               10.1039/c8ob00779a
_journal_volume                  16
_journal_year                    2018
_chemical_formula_moiety         '0.17(Br C15 O2)'
_chemical_formula_sum            'C H Br0 N O'
_chemical_formula_weight         43.03
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_primary     dual
_audit_creation_date             2018-03-22
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2018.01.22 svn.r3481 for OlexSys, GUI svn.r5457)
;
_audit_update_record
;
2018-04-02 deposited with the CCDC.
2018-05-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 116.689(8)
_cell_angle_gamma                90
_cell_formula_units_Z            23
_cell_length_a                   7.8543(5)
_cell_length_b                   20.6582(9)
_cell_length_c                   8.3912(5)
_cell_measurement_reflns_used    2364
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      72.2080
_cell_measurement_theta_min      4.3140
_cell_volume                     1216.46(15)
_computing_cell_refinement       'CrysAlisPro 1.171.39.29c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.29c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.29c (Rigaku OD, 2017)'
_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      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0802
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.968
_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     49.00  97.00   1.00   11.23    --   35.96  57.00   0.00   48
  2  \w     65.00 106.00   1.00   11.23    --   35.96 178.00 -30.00   41
  3  \w     65.00  93.00   1.00   11.23    --   35.96-178.00 120.00   28
  4  \w    -15.00  12.00   1.00   11.23    --   35.96 -77.00 150.00   27
  5  \w     17.00  62.00   1.00   11.23    --   35.96 -77.00 150.00   45
  6  \w     26.00  73.00   1.00   11.23    --   35.96  57.00 -30.00   47
  7  \w     -7.00  55.00   1.00   11.23    --   35.96 -38.00  30.00   62
  8  \w     39.00  94.00   1.00   44.92    --  108.00 -95.00-180.00   55
  9  \w    108.00 176.00   1.00   44.92    --  108.00  45.00 -60.00   68
 10  \w     64.00 115.00   1.00   44.92    --  108.00 -77.00 -90.00   51
 11  \w     93.00 126.00   1.00   44.92    --  108.00  61.00 -90.00   33
 12  \w     90.00 144.00   1.00   44.92    --  108.00  61.00-180.00   54
 13  \w     96.00 175.00   1.00   44.92    --  108.00  61.00  30.00   79
 14  \w     51.00  88.00   1.00   44.92    --  108.00 -95.00 -90.00   37
 15  \w     65.00 137.00   1.00   44.92    --  108.00 178.00-150.00   72
;
_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      0.0177471000
_diffrn_orient_matrix_UB_12      -0.0700110000
_diffrn_orient_matrix_UB_13      0.0690406000
_diffrn_orient_matrix_UB_21      -0.1838073000
_diffrn_orient_matrix_UB_22      -0.0183964000
_diffrn_orient_matrix_UB_23      -0.1667764000
_diffrn_orient_matrix_UB_31      0.1187694000
_diffrn_orient_matrix_UB_32      -0.0179399000
_diffrn_orient_matrix_UB_33      -0.0980277000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0138
_diffrn_reflns_av_unetI/netI     0.0153
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            4094
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.090
_diffrn_reflns_theta_min         4.280
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.073
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.28377
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.29c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_F_000             506
_refine_diff_density_max         7.012
_refine_diff_density_min         -5.863
_refine_diff_density_rms         0.319
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   6.194
_refine_ls_hydrogen_treatment    undef
_refine_ls_matrix_type           full
_refine_ls_number_parameters     73
_refine_ls_number_reflns         2329
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      6.194
_refine_ls_R_factor_all          0.2157
_refine_ls_R_factor_gt           0.2119
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.6061
_refine_ls_wR_factor_ref         0.6139
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2180
_reflns_number_total             2329
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ob00779a2.cif
_cod_data_source_block           20180321-1
_cod_depositor_comments          'Adding full bibliography for 7156270.cif.'
_cod_original_cell_volume        1216.46(14)
_cod_database_code               7156270
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C H O N'
_chemical_oxdiff_usercomment     'C H N S Ni'
_reflns_odcompleteness_completeness 99.51
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
;
_olex2_date_sample_data_collection 2018-03-21
_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 2.539
_oxdiff_exptl_absorpt_empirical_full_min 0.681