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_7122324
_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         'C15 H17 Cl N2 O5 S'
_chemical_formula_sum            'C15 H17 Cl N2 O5 S'
_chemical_formula_weight         372.82
_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             2018-04-20
_audit_creation_method
;
Olex2 1.2
(compiled 2018.04.18 svn.r3501 for OlexSys, GUI svn.r5488)
;
_audit_update_record
;
2018-05-21 deposited with the CCDC.
2018-09-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.412(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.5374(3)
_cell_length_b                   10.4577(3)
_cell_length_c                   18.7809(6)
_cell_measurement_reflns_used    4028
_cell_measurement_temperature    100
_cell_measurement_theta_max      75.2270
_cell_measurement_theta_min      4.7250
_cell_volume                     1662.78(9)
_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 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  68.00   1.00    2.00    --   44.06 -37.00   0.00   92
  2  \w      7.00  97.00   1.00    2.00    --   44.06-125.00 -30.00   90
  3  \w     54.00 134.00   1.00    6.00    --  107.00 -61.00-120.00   80
  4  \w     76.00 178.00   1.00    6.00    --  107.00  77.00  30.00  102
  5  \w    135.00 164.00   1.00    6.00    --  107.00  45.00 150.00   29
  6  \w     83.00 112.00   1.00    6.00    --  107.00  45.00 150.00   29
  7  \w     95.00 169.00   1.00    6.00    --  107.00  77.00 -60.00   74
  8  \w     33.00 103.00   1.00    6.00    --  107.00-125.00-120.00   70
  9  \w   -119.00 -79.00   1.00    2.00    --  -44.06 -99.00   0.00   40
;
_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      0.1413124000
_diffrn_orient_matrix_UB_12      -0.0878884000
_diffrn_orient_matrix_UB_13      0.0248715000
_diffrn_orient_matrix_UB_21      0.1096829000
_diffrn_orient_matrix_UB_22      0.0895975000
_diffrn_orient_matrix_UB_23      -0.0360168000
_diffrn_orient_matrix_UB_31      0.0336812000
_diffrn_orient_matrix_UB_32      0.0772176000
_diffrn_orient_matrix_UB_33      0.0701158000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0328
_diffrn_reflns_av_unetI/netI     0.0334
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            6037
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.058
_diffrn_reflns_theta_max         67.058
_diffrn_reflns_theta_min         4.749
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Nova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.473
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.23037
_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    1.489
_exptl_crystal_description       block
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.366
_refine_diff_density_min         -0.335
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         2968
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.0448
_refine_ls_R_factor_gt           0.0417
_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^)+(0.0573P)^2^+1.1014P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1093
_refine_ls_wR_factor_ref         0.1116
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2730
_reflns_number_total             2968
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8cc06807k2.cif
_cod_data_source_block           hxl_180420
_cod_depositor_comments
'Adding full bibliography for 7122323--7122324.cif.'
_cod_original_cell_volume        1662.79(9)
_cod_database_code               7122324
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.723
_shelx_estimated_absorpt_t_min   0.422
_reflns_odcompleteness_completeness 99.78
_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:
 C18(H18A,H18B), C19(H19A,H19B), C22(H22A,H22B)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C9(H9), C14(H14), C17(H17), C20(H20)
2.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C21(H21A,H21B,H21C)
;
_shelx_res_checksum              72744
_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 4.257
_oxdiff_exptl_absorpt_empirical_full_min 0.452