A phosphine free, inorganic base free, one-pot tandem Mizoroki–Heck olefination/direct arylation/hydrogenation sequence, to give multicyclic alkylated heteroarenes
Kehoe, Roberta A.; Light, Mark E.; Jones, David J.; McGlacken, Gerard P.; Green Chemistry 25 (2023) 5654–5660; doi:10.1039/D3GC01403G

data_7246951
_publ_section_title
;
 A phosphine free, inorganic base free, one-pot tandem Mizoroki--Heck
 olefination/direct arylation/hydrogenation sequence, to give multicyclic
 alkylated heteroarenes
;
_journal_issue                   14
_journal_name_full               'Green Chemistry'
_journal_page_first              5654
_journal_page_last               5660
_journal_paper_doi               10.1039/D3GC01403G
_journal_volume                  25
_journal_year                    2023
_chemical_formula_moiety         'C23 H17 N O'
_chemical_formula_sum            'C23 H17 N O'
_chemical_formula_weight         323.38
_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             2022-01-20
_audit_creation_method
;
Olex2 1.5-alpha
(compiled 2021.12.21 svn.raa29eb21 for OlexSys, GUI svn.r6440)
;
_audit_update_record
;
2022-01-20 deposited with the CCDC.	2023-06-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.5230(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.80750(10)
_cell_length_b                   27.2149(4)
_cell_length_c                   12.4496(2)
_cell_measurement_reflns_used    8715
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.1850
_cell_measurement_theta_min      3.8870
_cell_volume                     1627.27(5)
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.956
_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    -68.00  11.00   0.50    0.76    --  -45.19  84.00-124.00  158
  2  \w    -17.00  68.00   0.50    0.76    --   45.19 -84.00 115.00  170
  3  \w    -91.00 -23.00   0.50    3.03    --  -97.00  84.00-124.00  136
  4  \w   -170.00-106.00   0.50    3.03    --  -97.00 -84.00 115.00  128
  5  \w     99.00 175.00   0.50    3.03    --  109.75  84.00-124.00  152
  6  \w     37.00  85.00   0.50    3.03    --  109.75 -84.00 115.00   96
  7  \w   -120.00 -39.00   0.50    0.76    --  -45.19 -38.00  30.00  162
  8  \w    -27.00  42.00   0.50    0.76    --   45.19 -57.00 -30.00  138
  9  \w    -30.00  16.00   0.50    0.76    --   45.19 -38.00   0.00   92
 10  \w    -30.00  16.00   0.50    0.76    --   45.19 -38.00  30.00   92
 11  \w   -139.00 -90.00   0.50    3.03    --  -97.00 -15.00 120.00   98
 12  \w   -139.00 -90.00   0.50    3.03    --  -97.00 -15.00 -90.00   98
 13  \w   -139.00 -90.00   0.50    3.03    --  -97.00 -15.00  90.00   98
 14  \w    -54.00 -23.00   0.50    3.03    --  -97.00  61.00-120.00   62
 15  \w    -54.00 -23.00   0.50    3.03    --  -97.00  61.00 120.00   62
 16  \w    -54.00 -23.00   0.50    3.03    --  -97.00  61.00  60.00   62
 17  \w    -54.00 -23.00   0.50    3.03    --  -97.00  61.00-150.00   62
 18  \w     37.00  72.00   0.50    3.03    --  109.75 -77.00-180.00   70
 19  \w    104.00 133.00   0.50    3.03    --  109.75  15.00   0.00   58
 20  \w    104.00 133.00   0.50    3.03    --  109.75  15.00-120.00   58
 21  \w     37.00  72.00   0.50    3.03    --  109.75 -77.00 -90.00   70
 22  \w     37.00  72.00   0.50    3.03    --  109.75 -77.00  30.00   70
 23  \w    104.00 133.00   0.50    3.03    --  109.75  15.00  60.00   58
 24  \w    104.00 163.00   0.50    3.03    --  109.75  30.00-180.00  118
 25  \w     37.00  72.00   0.50    3.03    --  109.75 -77.00   0.00   70
 26  \w     37.00  72.00   0.50    3.03    --  109.75 -77.00 150.00   70
 27  \w    104.00 163.00   0.50    3.03    --  109.75  30.00   0.00  118
 28  \w   -120.00 -39.00   0.50    0.76    --  -45.19 -38.00 120.00  162
 29  \w   -120.00 -39.00   0.50    0.76    --  -45.19 -38.00-150.00  162
 30  \w   -120.00 -39.00   0.50    0.76    --  -45.19 -38.00 -60.00  162
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1516700000
_diffrn_orient_matrix_UB_12      -0.0495689000
_diffrn_orient_matrix_UB_13      0.0145108000
_diffrn_orient_matrix_UB_21      -0.0200761000
_diffrn_orient_matrix_UB_22      0.0042944000
_diffrn_orient_matrix_UB_23      0.1228206000
_diffrn_orient_matrix_UB_31      -0.2819344000
_diffrn_orient_matrix_UB_32      -0.0269775000
_diffrn_orient_matrix_UB_33      -0.0071445000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0347
_diffrn_reflns_av_unetI/netI     0.0264
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.956
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            15653
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.956
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.365
_diffrn_reflns_theta_min         3.248
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.628
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84299
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_description       needle
_exptl_crystal_F_000             680
_exptl_crystal_recrystallization_method
'The material was recrystallised from methanol by slow evaporation'
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.177
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3254
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0454
_refine_ls_R_factor_gt           0.0402
_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^)+(0.0313P)^2^+0.7901P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0932
_refine_ls_wR_factor_ref         0.0957
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2923
_reflns_number_total             3254
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3gc01403g2.cif
_cod_data_source_block           2021acc0020_d1_100k
_cod_depositor_comments
'Adding full bibliography for 7246950--7246958.cif.'
_cod_database_code               7246951
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C12 H12 N1 O1'
_chemical_oxdiff_usercomment     'RAK-398 MeOH'
_shelx_estimated_absorpt_t_max   0.988
_shelx_estimated_absorpt_t_min   0.864
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C17(H17A,H17B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C7(H7), C12(H12), C14(H14), C15(H15),
 C19(H19), C20(H20), C21(H21), C22(H22), C23(H23)
;
_shelx_res_checksum              34908
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a MITIGEN holder with silicon oil'
_olex2_submission_original_sample_id 'RAK-398 MeOH'
_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 1.528
_oxdiff_exptl_absorpt_empirical_full_min 0.803