Heck-Suzuki Tandem Reaction for the Synthesis of 3-Benzazepines.
Peshkov, Anatoly A.; Peshkov, Vsevolod A.; Pereshivko, Olga P.; Van Hecke, Kristof; Kumar, Rakesh; V Van der Eycken, Erik; The Journal of organic chemistry 80 (2015) 6598–6608; doi:10.1021/acs.joc.5b00670

data_4031108
_publ_section_title
;
 Heck-Suzuki Tandem Reaction for the Synthesis of 3-Benzazepines.
;
_journal_issue                   13
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              6598
_journal_page_last               6608
_journal_paper_doi               10.1021/acs.joc.5b00670
_journal_volume                  80
_journal_year                    2015
_chemical_formula_moiety         'C29 H31 N O4'
_chemical_formula_sum            'C29 H31 N O4'
_chemical_formula_weight         457.55
_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
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-04-04
_audit_creation_method
;
  Olex2 1.2-ac2
  (compiled 2012.03.27 svn.r2268, GUI svn.r4156)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 105.549(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.6205(2)
_cell_length_b                   11.36761(17)
_cell_length_c                   19.4826(4)
_cell_measurement_reflns_used    8181
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      75.2098
_cell_measurement_theta_min      3.8854
_cell_volume                     2479.41(8)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean 10.4839
_diffrn_measured_fraction_theta_full 0.9994
_diffrn_measured_fraction_theta_max 0.9994
_diffrn_measurement_details
;
  1 omega   52.00   78.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.8048   52.0000  -95.0000 26

  2 omega   15.00  112.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.8048   52.0000 -119.0000 97

  3 omega    0.00   28.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.8048  -52.0000  -60.0000 28

  4 omega  -42.00  -17.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.5000   52.0000   60.0000 25

  5 omega  -56.00   29.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.5000   52.0000   84.0000 85

  6 omega -103.00  -65.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.5000  -52.0000   95.0000 38

  7 omega  -96.00  -16.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.5000  -52.0000  119.0000 80

  8 omega   55.00   97.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316  -52.0000  -60.0000 42

  9 omega  137.00  166.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316   52.0000  -95.0000 29

 10 omega   37.00   66.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316  -52.0000  -84.0000 29

 11 omega   83.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316   52.0000 -119.0000 95

 12 omega  -43.00  -18.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.5000  -45.0000  -60.0000 25

 13 omega -118.00  -81.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.5000  -94.0000 -150.0000 37

 14 omega -116.00  -19.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.5000  -45.0000    0.0000 97

 15 omega   38.00  120.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316 -125.0000 -180.0000 82

 16 omega   74.00   99.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316  -94.0000 -120.0000 25

 17 omega   80.00  107.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316   61.0000    0.0000 27

 18 omega   26.00   57.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316  -94.0000 -120.0000 31

 19 omega   80.00  111.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316   61.0000   30.0000 31

 20 omega  116.00  158.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316   61.0000   30.0000 42

 21 omega   77.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316   77.0000  -30.0000 26

 22 omega  123.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316   77.0000  -30.0000 55

 23 omega   85.00  159.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316   45.0000   60.0000 74

 24 omega   77.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316   77.0000    0.0000 26

 25 omega   40.00   69.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316  -30.0000  -90.0000 29

 26 omega   35.00   86.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316  -30.0000  -30.0000 51

 27 omega   82.00  109.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316   61.0000  -30.0000 27

 28 omega   83.00  109.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316   45.0000   30.0000 26

 29 omega  124.00  149.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316   61.0000    0.0000 25

 30 omega   83.00  110.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316   45.0000    0.0000 27

 31 omega   78.00  166.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316   77.0000  -60.0000 88

 32 omega   82.00  107.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316   30.0000   30.0000 25

 33 omega   47.00   94.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316  -94.0000 -180.0000 47
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0484756000
_diffrn_orient_matrix_UB_12      -0.0839722000
_diffrn_orient_matrix_UB_13      0.0632835000
_diffrn_orient_matrix_UB_21      -0.1276199000
_diffrn_orient_matrix_UB_22      -0.0174960000
_diffrn_orient_matrix_UB_23      0.0073934000
_diffrn_orient_matrix_UB_31      -0.0174120000
_diffrn_orient_matrix_UB_32      -0.1049012000
_diffrn_orient_matrix_UB_33      -0.0517368000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0272
_diffrn_reflns_av_unetI/netI     0.0190
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            22367
_diffrn_reflns_theta_full        75.39
_diffrn_reflns_theta_max         75.39
_diffrn_reflns_theta_min         3.95
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.648
_exptl_absorpt_correction_T_max  0.985
_exptl_absorpt_correction_T_min  0.971
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Analytical numeric absorption correction using a multifaceted crystal
            model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.226
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             976
_exptl_crystal_size_max          0.3216
_exptl_crystal_size_mid          0.1896
_exptl_crystal_size_min          0.1059
_refine_diff_density_max         0.164
_refine_diff_density_min         -0.139
_refine_diff_density_rms         0.030
_refine_ls_extinction_coef       0.0018(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     312
_refine_ls_number_reflns         5081
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0507
_refine_ls_R_factor_gt           0.0403
_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^)+(0.0614P)^2^+0.3195P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1074
_refine_ls_wR_factor_ref         0.1175
_reflns_number_gt                4075
_reflns_number_total             5081
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo5b00670_si_002.cif
_cod_data_source_block           evde_ugent001
_cod_depositor_comments
'Adding full bibliography for 4031105--4031108.cif.'
_cod_database_code               4031108
_chemical_oxdiff_formula         'C29 H31 N1 O4'
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97