Palladium-Catalyzed Regioselective C-H Acylation of Biaryl-2-amines.
Cai, Zhong-Jian; Yang, Chao; Wang, Shun-Yi; Ji, Shun-Jun; The Journal of organic chemistry 80 (2015) 7928–7936; doi:10.1021/acs.joc.5b00962

data_4036228
_publ_section_title
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 Palladium-Catalyzed Regioselective C-H Acylation of Biaryl-2-amines.
;
_journal_issue                   16
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              7928
_journal_page_last               7936
_journal_paper_doi               10.1021/acs.joc.5b00962
_journal_volume                  80
_journal_year                    2015
_chemical_formula_moiety         'C26 H21 N O3 S'
_chemical_formula_sum            'C26 H21 N O3 S'
_chemical_formula_weight         427.50
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-09-15
_audit_creation_method
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Olex2 1.2
(compiled 2014.02.28 svn.r2899 for OlexSys, GUI svn.r4781)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 105.976(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.3326(7)
_cell_length_b                   19.2076(9)
_cell_length_c                   11.4445(7)
_cell_measurement_reflns_used    3257
_cell_measurement_temperature    223.00(10)
_cell_measurement_theta_max      27.6130
_cell_measurement_theta_min      3.1490
_cell_volume                     2183.6(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      223.00(10)
_diffrn_detector_area_resol_mean 10.4471
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0103026000
_diffrn_orient_matrix_UB_12      0.0365285000
_diffrn_orient_matrix_UB_13      -0.0034807000
_diffrn_orient_matrix_UB_21      -0.0652388000
_diffrn_orient_matrix_UB_22      -0.0047181000
_diffrn_orient_matrix_UB_23      0.0077803000
_diffrn_orient_matrix_UB_31      0.0272802000
_diffrn_orient_matrix_UB_32      0.0025501000
_diffrn_orient_matrix_UB_33      0.0638797000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0322
_diffrn_reflns_av_unetI/netI     0.0423
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            12283
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         3.12
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.176
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77899
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.300
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.6
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.286
_refine_diff_density_min         -0.457
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         4448
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.0704
_refine_ls_R_factor_gt           0.0488
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1405
_refine_ls_wR_factor_ref         0.1596
_reflns_number_gt                3291
_reflns_number_total             4448
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo5b00962_si_002.cif
_cod_data_source_block           g140915a
_cod_database_code               4036228
_chemical_oxdiff_formula         'C11 H10 N O'
_reflns_odcompleteness_completeness 99.74
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Riding coordinates:
 N1(H1)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1A), C2(H2), C4(H4), C5(H5), C9(H9), C10(H10), C11(H11), C12(H12),
 C15(H15), C16(H16), C17(H17), C18(H18), C22(H22), C23(H23), C24(H24), C25(H25),
  C26(H26)
2.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C)
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