Cp*Co(iii)-Catalyzed oxidative [5+2] annulation: regioselective synthesis of 2-aminobenzoxepines via C-H/O-H functionalization of 2-vinylphenols with ynamides.
Han, Xiang-Lei; Liu, Xu-Ge; Lin, E.; Chen, Yunyun; Chen, Zhuangzhong; Wang, Honggen; Li, Qingjiang; Chemical communications (Cambridge, England) 54 (2018) 11562–11565; doi:10.1039/c8cc06807k

data_7122323
_publ_section_title
;
 Cp*Co(iii)-Catalyzed oxidative [5+2] annulation: regioselective synthesis
 of 2-aminobenzoxepines via C-H/O-H functionalization of 2-vinylphenols
 with ynamides.
;
_journal_issue                   82
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              11562
_journal_page_last               11565
_journal_paper_doi               10.1039/c8cc06807k
_journal_volume                  54
_journal_year                    2018
_chemical_formula_moiety         'C20 H21 N O3 S'
_chemical_formula_sum            'C20 H21 N O3 S'
_chemical_formula_weight         355.44
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2018-01-29
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2018-05-21 deposited with the CCDC.
2018-09-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.489(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.5862(3)
_cell_length_b                   9.9930(2)
_cell_length_c                   13.1956(3)
_cell_measurement_reflns_used    4944
_cell_measurement_temperature    100
_cell_measurement_theta_max      75.3870
_cell_measurement_theta_min      3.2380
_cell_volume                     1786.03(7)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)'
_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      100
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.2417
_diffrn_detector_type            Onyx
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_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    -24.00  64.00   1.00    2.00    --   44.06 -57.00-120.00   88
  2  \w    124.00 176.00   1.00    5.00    --  107.00  30.00 -60.00   52
  3  \w     88.00 114.00   1.00    5.00    --  107.00 125.00   0.00   26
  4  \w     80.00 174.00   1.00    5.00    --  107.00  61.00  60.00   94
  5  \w     99.00 177.00   1.00    5.00    --  107.00  77.00 150.00   78
  6  \w     77.00 109.00   1.00    5.00    --  107.00 -94.00 150.00   32
  7  \w     25.00  50.00   1.00    5.00    --  107.00 -94.00 150.00   25
  8  \w     33.00 124.00   1.00    5.00    --  107.00 -77.00 -60.00   91
  9  \w     21.00 112.00   1.00    2.00    --   44.06  57.00  30.00   91
 10  \w    -10.00  16.00   1.00    2.00    --  -44.06  77.00 150.00   26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Onyx, Nova'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0308994000
_diffrn_orient_matrix_UB_12      -0.1423964000
_diffrn_orient_matrix_UB_13      0.0342039000
_diffrn_orient_matrix_UB_21      0.1053913000
_diffrn_orient_matrix_UB_22      0.0270049000
_diffrn_orient_matrix_UB_23      -0.0303163000
_diffrn_orient_matrix_UB_31      0.0295636000
_diffrn_orient_matrix_UB_32      0.0525549000
_diffrn_orient_matrix_UB_33      0.1078257000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0200
_diffrn_reflns_av_unetI/netI     0.0232
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6433
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.080
_diffrn_reflns_theta_max         67.080
_diffrn_reflns_theta_min         3.263
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Nova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.762
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.51968
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41r (Rigaku Oxford Diffraction, 2015)
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    1.322
_exptl_crystal_description       block
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.273
_refine_diff_density_min         -0.345
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3164
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0360
_refine_ls_R_factor_gt           0.0343
_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^)+(0.0489P)^2^+0.6945P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0920
_refine_ls_wR_factor_ref         0.0933
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2979
_reflns_number_total             3164
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8cc06807k2.cif
_cod_data_source_block           hxl_180125
_cod_depositor_comments
'Adding full bibliography for 7122323--7122324.cif.'
_cod_database_code               7122323
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.844
_shelx_estimated_absorpt_t_min   0.620
_reflns_odcompleteness_completeness 99.26
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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
2.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C24(H24A,H24B)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C10(H10), C11(H11), C13(H13), C14(H14), C17(H17), C18(H18),
 C19(H19), C21(H21), C23(H23)
2.c Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C22(H22A,H22B,H22C)
;
_shelx_res_checksum              24661
_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 1.682
_oxdiff_exptl_absorpt_empirical_full_min 0.682