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_4031105
_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         'C21 H19 N O'
_chemical_formula_sum            'C21 H19 N O'
_chemical_formula_weight         301.37
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
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_audit_creation_date             2014-02-03
_audit_creation_method
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Olex2 1.2
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_cell_length_b                   11.5783(5)
_cell_length_c                   28.3556(13)
_cell_measurement_reflns_used    8733
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      75.9420
_cell_measurement_theta_min      4.6820
_cell_volume                     3158.2(2)
_computing_cell_refinement
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
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_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
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_diffrn_ambient_environment      N~2~
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_diffrn_detector                 'CCD plate'
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  1 omega   33.00   65.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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  2 omega   53.00  100.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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  3 omega   56.00  102.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000 -143.0000 -157.0000 46

  4 omega   65.00   90.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -60.0000 -113.0000 25

  5 omega  112.00  143.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   60.0000 -147.0000 31

  6 omega   43.00   81.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000 -127.0000   12.0000 38

  7 omega -114.00  -89.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.8048 -143.0000 -157.0000 25

  8 omega   69.00   98.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.8048 -143.0000 -157.0000 29

  9 omega -124.00  -88.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.5000  -94.0000  150.0000 36

 10 omega -126.00  -97.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.5000  -94.0000  -60.0000 29

 11 omega -111.00  -80.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.5000  -94.0000   30.0000 31

 12 omega   48.00  120.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000 -125.0000   90.0000 72

 13 omega   83.00  164.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   61.0000 -180.0000 81

 14 omega   63.00   97.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -45.0000 -120.0000 34

 15 omega   38.00   98.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -45.0000   30.0000 60

 16 omega   36.00   83.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -30.0000  -60.0000 47

 17 omega   77.00  109.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -94.0000   60.0000 32

 18 omega -114.00  -14.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.8048  -57.0000  150.0000 100

 19 omega  -50.00   32.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.8048   38.0000  -90.0000 82

 20 omega -118.00   -9.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.8048  -77.0000  -60.0000 109

 21 omega   82.00  116.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   60.0000   26.0000 34
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_diffrn_measurement_device       'four-circle diffractometer'
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_diffrn_orient_matrix_UB_11      -0.0812475000
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_diffrn_orient_matrix_UB_21      0.0787403000
_diffrn_orient_matrix_UB_22      -0.0570866000
_diffrn_orient_matrix_UB_23      0.0411836000
_diffrn_orient_matrix_UB_31      0.1133488000
_diffrn_orient_matrix_UB_32      0.0936044000
_diffrn_orient_matrix_UB_33      -0.0033222000
_diffrn_radiation_monochromator  mirror
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_diffrn_radiation_type           CuK\a
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_diffrn_reflns_av_unetI/netI     0.0297
_diffrn_reflns_Laue_measured_fraction_full 0.995
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_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            16122
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.485
_diffrn_reflns_theta_min         3.117
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.602
_exptl_absorpt_correction_T_max  0.991
_exptl_absorpt_correction_T_min  0.979
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_exptl_absorpt_process_details
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Numerical absorption correction based on gaussian integration over
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Empirical absorption correction using spherical harmonics,
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_exptl_crystal_colour            colourless
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_exptl_crystal_description       block
_exptl_crystal_F_000             1280
_exptl_crystal_size_max          0.3599
_exptl_crystal_size_mid          0.2038
_exptl_crystal_size_min          0.1469
_refine_diff_density_max         0.224
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_refine_ls_extinction_coef       0.00123(13)
_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   1.049
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         3203
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0530
_refine_ls_R_factor_gt           0.0418
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0474P)^2^+1.1629P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
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_cod_depositor_comments
'Adding full bibliography for 4031105--4031108.cif.'
_cod_database_code               4031105
_shelxl_version_number           2013-4
_chemical_oxdiff_formula         'C21 H19 N O'
_reflns_odcompleteness_completeness 99.69
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
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1. Others
 Fixed Uiso: H5A(0.023) H5B(0.023) H6A(0.022) H6B(0.022) H7(0.023) H8(0.026)
 H9(0.027) H10(0.025) H11A(0.033) H11B(0.033) H11C(0.033) H13A(0.031)
 H13B(0.031) H13C(0.031) H17(0.027) H18(0.033) H19(0.034) H20(0.032) H21(0.028)
 Fixed X: H5A(1.1309) H5B(1.1237) H6A(1.3072) H6B(1.1907) H7(0.7275)
 H8(0.5725) H9(0.656) H10(0.8943) H11A(1.4011) H11B(1.3035) H11C(1.2809)
 H13A(1.0846) H13B(1.1523) H13C(1.0114) H17(0.6842) H18(0.526) H19(0.4539)
 H20(0.5426) H21(0.7)
 Fixed Y: H5A(0.741) H5B(0.8076) H6A(0.6799) H6B(0.6351) H7(0.5094) H8(0.6503)
 H9(0.8231) H10(0.852) H11A(0.51) H11B(0.5861) H11C(0.4494) H13A(0.3375)
 H13B(0.3368) H13C(0.2673) H17(0.4101) H18(0.4863) H19(0.6777) H20(0.7964)
 H21(0.7215)
 Fixed Z: H5A(0.2868) H5B(0.336) H6A(0.3395) H6B(0.3754) H7(0.3607) H8(0.3355)
 H9(0.3029) H10(0.296) H11A(0.291) H11B(0.2575) H11C(0.2608) H13A(0.4485)
 H13B(0.3969) H13C(0.4067) H17(0.5392) H18(0.5934) H19(0.5875) H20(0.528)
 H21(0.4731)
;