Trifunctionalization of Allenes via Cobalt-Catalyzed MHP-Assisted C–H Bond Functionalization and Molecular Oxygen Activation
Zhai, Shengxian; Qiu, Shuxian; Chen, Xiaoming; Tao, Cheng; Li, Yun; Cheng, Bin; Wang, Huifei; Zhai, Hongbin; ACS Catalysis 8 (2018) 6645–; doi:10.1021/acscatal.8b01720

data_4515680
_publ_section_title
;
 Trifunctionalization of Allenes via Cobalt-Catalyzed MHP-Assisted C--H
 Bond Functionalization and Molecular Oxygen Activation
;
_journal_issue                   7
_journal_name_full               'ACS Catalysis'
_journal_page_first              6645
_journal_paper_doi               10.1021/acscatal.8b01720
_journal_volume                  8
_journal_year                    2018
_chemical_formula_moiety         'C22 H17 N3 O2'
_chemical_formula_sum            'C22 H17 N3 O2'
_chemical_formula_weight         355.38
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-11-16
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                90
_cell_angle_beta                 93.713(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.0252(3)
_cell_length_b                   14.9032(8)
_cell_length_c                   19.2088(12)
_cell_measurement_reflns_used    4875
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      28.8700
_cell_measurement_theta_min      2.7210
_cell_volume                     1721.23(17)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.978
_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    -35.00  54.00   1.00    2.45    --  -11.59  57.00-120.00   89
  2  \w    -80.00  20.00   1.00    2.45    --  -11.59 -77.00 -30.00  100
  3  \w    -84.00  17.00   1.00    2.45    --  -11.59 -57.00  90.00  101
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0717755000
_diffrn_orient_matrix_UB_12      0.0334868000
_diffrn_orient_matrix_UB_13      -0.0120604000
_diffrn_orient_matrix_UB_21      0.0129621000
_diffrn_orient_matrix_UB_22      0.0182344000
_diffrn_orient_matrix_UB_23      0.0341632000
_diffrn_orient_matrix_UB_31      0.0927409000
_diffrn_orient_matrix_UB_32      -0.0284290000
_diffrn_orient_matrix_UB_33      0.0076334000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0637
_diffrn_reflns_av_unetI/netI     0.0529
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            9654
_diffrn_reflns_point_group_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        24.994
_diffrn_reflns_theta_max         24.994
_diffrn_reflns_theta_min         2.125
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.18410
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (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    1.371
_exptl_crystal_description       block
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.219
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         2960
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0543
_refine_ls_R_factor_gt           0.0446
_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^)+(0.0639P)^2^+0.2658P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1143
_refine_ls_wR_factor_ref         0.1252
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2504
_reflns_number_total             2960
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs8b01720_si_002.cif
_cod_data_source_block           exp_975
_cod_database_code               4515680
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.989
_shelx_estimated_absorpt_t_min   0.984
_reflns_odcompleteness_completeness 96.79
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C2(H2), C16(H16), C19(H19), C5(H5), C4(H4), C22(H22), C3(H3),
 C15(H15), C12(H12), C14(H14), C13(H13), C20(H20), C21(H21)
2.b Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C)
;
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 6.361
_oxdiff_exptl_absorpt_empirical_full_min 0.552