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_4031107
_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 H25 N O'
_chemical_formula_sum            'C29 H25 N O'
_chemical_formula_weight         403.50
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2014-02-04
_audit_creation_method
;
Olex2 1.2
(compiled 2013.12.10 svn.r2853 for OlexSys, GUI svn.r4736)
;
_cell_angle_alpha                69.827(7)
_cell_angle_beta                 77.025(6)
_cell_angle_gamma                74.068(7)
_cell_formula_units_Z            4
_cell_length_a                   9.9850(7)
_cell_length_b                   14.3686(13)
_cell_length_c                   16.9433(9)
_cell_measurement_reflns_used    4552
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      74.8530
_cell_measurement_theta_min      3.3360
_cell_volume                     2171.3(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
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_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.97(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4839
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details
;
  1 omega   -4.00   21.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.6798  -63.0000   79.0000 25

  2 omega   39.00   64.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.6798   63.0000 -143.0000 25

  3 omega  -73.00   27.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.5000   63.0000 -143.0000 100

  4 omega -106.00  -28.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.5000  -63.0000   79.0000 78

  5 omega   74.00  101.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -63.0000   79.0000 27

  6 omega  145.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   63.0000 -143.0000 33

  7 omega   23.00   81.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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  8 omega   48.00   75.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.6798 -125.0000  -90.0000 27

  9 omega    3.00   83.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.6798  -99.0000   30.0000 80

 10 omega -123.00  -80.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.5000  -94.0000 -180.0000 43

 11 omega -124.00  -81.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.5000  -94.0000  120.0000 43

 12 omega -112.00  -87.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.5000  -94.0000 -150.0000 25

 13 omega   58.00  114.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000 -125.0000  -90.0000 56

 14 omega   64.00   90.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -30.0000 -120.0000 26

 15 omega   97.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   30.0000  150.0000 81

 16 omega   76.00  164.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -15.0000  120.0000 88

 17 omega  111.00  144.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -77.0000 -150.0000 33

 18 omega   49.00   78.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -45.0000  -30.0000 29

 19 omega   44.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -94.0000  -90.0000 59

 20 omega   42.00   68.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000 -125.0000 -150.0000 26

 21 omega   93.00  172.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   61.0000 -180.0000 79

 22 omega   37.00   62.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -15.0000  120.0000 25

 23 omega   96.00  121.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000 -125.0000   90.0000 25

 24 omega   40.00   76.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000 -125.0000   90.0000 36

 25 omega   44.00  120.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000 -125.0000   30.0000 76

 26 omega   88.00  121.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000 -125.0000 -150.0000 33

 27 omega   39.00  140.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -61.0000  120.0000 101

 28 omega   78.00  105.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -77.0000 -150.0000 27

 29 omega   47.00  101.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -94.0000   90.0000 54

 30 omega  110.00  136.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  125.0000 -180.0000 26

 31 omega  138.00  169.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  125.0000 -180.0000 31

 32 omega  104.00  129.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  125.0000   30.0000 25

 33 omega   39.00   87.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000 -125.0000   60.0000 48

 34 omega   28.00   89.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -94.0000  120.0000 61

 35 omega   43.00   69.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -61.0000 -180.0000 26

 36 omega   95.00  121.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -61.0000 -180.0000 26

 37 omega   62.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -94.0000   30.0000 41

 38 omega  118.00  145.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   45.0000  -60.0000 27

 39 omega   39.00   96.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -45.0000 -120.0000 57

 40 omega -115.00  -14.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.6798  -57.0000 -180.0000 101

 41 omega -115.00  -14.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.6798  -57.0000    0.0000 101

 42 omega -118.00   -9.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.6798  -77.0000  -60.0000 109
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.1383715000
_diffrn_orient_matrix_UB_12      0.0109157000
_diffrn_orient_matrix_UB_13      -0.0612486000
_diffrn_orient_matrix_UB_21      0.0612592000
_diffrn_orient_matrix_UB_22      -0.1139984000
_diffrn_orient_matrix_UB_23      0.0382955000
_diffrn_orient_matrix_UB_31      -0.0582186000
_diffrn_orient_matrix_UB_32      -0.0238207000
_diffrn_orient_matrix_UB_33      -0.0660571000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.1031
_diffrn_reflns_av_unetI/netI     0.1262
_diffrn_reflns_Laue_measured_fraction_full 0.967
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            24679
_diffrn_reflns_point_group_measured_fraction_full 0.967
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         66.599
_diffrn_reflns_theta_min         3.668
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.571
_exptl_absorpt_correction_T_max  0.991
_exptl_absorpt_correction_T_min  0.978
_exptl_absorpt_correction_type   gaussian
_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
            a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.234
_exptl_crystal_description       block
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.2572
_exptl_crystal_size_mid          0.157
_exptl_crystal_size_min          0.1056
_refine_diff_density_max         0.413
_refine_diff_density_min         -0.353
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_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.959
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     563
_refine_ls_number_reflns         7602
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.959
_refine_ls_R_factor_all          0.1439
_refine_ls_R_factor_gt           0.0651
_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^)+(0.0838P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1483
_refine_ls_wR_factor_ref         0.1964
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4008
_reflns_number_total             7602
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo5b00670_si_005.cif
_cod_data_source_block           evde_ugent005
_cod_depositor_comments
'Adding full bibliography for 4031105--4031108.cif.'
_cod_database_code               4031107
_shelxl_version_number           2013-4
_chemical_oxdiff_formula         'C29 H25 N O'
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H5A(0.04) H5B(0.04) H6A(0.039) H6B(0.039) H7(0.037) H8(0.038)
 H9(0.039) H10(0.038) H11A(0.061) H11B(0.061) H11C(0.061) H13A(0.048)
 H13B(0.048) H13C(0.048) H14(0.034) H17(0.037) H18(0.041) H19(0.045) H20(0.042)
 H21(0.035) H25(0.043) H26(0.046) H27(0.047) H28(0.044) H29(0.041) H34A(0.037)
 H34B(0.037) H35A(0.039) H35B(0.039) H36(0.037) H37(0.038) H38(0.041)
 H39(0.039) H40A(0.055) H40B(0.055) H40C(0.055) H42A(0.052) H42B(0.052)
 H42C(0.052) H43(0.034) H46(0.037) H47(0.043) H48(0.043) H49(0.041) H50(0.039)
 H54(0.044) H55(0.045) H56(0.047) H57(0.044) H58(0.043)
 Fixed X: H5A(0.9135) H5B(1.0343) H6A(0.9522) H6B(0.9956) H7(0.6084)
 H8(0.6288) H9(0.7763) H10(0.9037) H11A(0.7834) H11B(0.8074) H11C(0.6538)
 H13A(0.7683) H13B(0.605) H13C(0.6962) H14(0.8286) H17(0.5643) H18(0.4846)
 H19(0.6462) H20(0.8877) H21(0.9663) H25(0.9599) H26(1.1142) H27(1.3398)
 H28(1.4149) H29(1.2626) H34A(0.573) H34B(0.4567) H35A(0.5346) H35B(0.4849)
 H36(0.889) H37(0.8762) H38(0.7319) H39(0.5956) H40A(0.6512) H40B(0.8163)
 H40C(0.7208) H42A(0.7969) H42B(0.7247) H42C(0.888) H43(0.6704) H46(0.9308)
 H47(1.0126) H48(0.8529) H49(0.611) H50(0.5298) H54(0.5316) H55(0.3723)
 H56(0.1437) H57(0.0722) H58(0.2308)
 Fixed Y: H5A(1.2342) H5B(1.139) H6A(1.1523) H6B(1.255) H7(0.9776) H8(0.9169)
 H9(0.9756) H10(1.0925) H11A(1.3943) H11B(1.41) H11C(1.4066) H13A(1.0578)
 H13B(1.0806) H13C(1.164) H14(0.9194) H17(0.8979) H18(0.8854) H19(0.8391)
 H20(0.804) H21(0.8122) H25(0.5115) H26(0.3719) H27(0.3852) H28(0.5355)
 H29(0.6758) H34A(0.5414) H34B(0.5234) H35A(0.3459) H35B(0.3983) H36(0.3666)
 H37(0.5253) H38(0.6689) H39(0.6516) H40A(0.3554) H40B(0.3342) H40C(0.4457)
 H42A(0.1304) H42B(0.0808) H42C(0.0839) H43(0.3008) H46(0.0525) H47(-0.124)
 H48(-0.23) H49(-0.1595) H50(0.0144) H54(0.2493) H55(0.3241) H56(0.4024)
 H57(0.4063) H58(0.3295)
 Fixed Z: H5A(-0.0786) H5B(-0.0425) H6A(0.0967) H6B(0.0334) H7(0.1137) H8(-
 0.0008) H9(-0.1262) H10(-0.1364) H11A(-0.0334) H11B(0.051) H11C(0.0402)
 H13A(0.3279) H13B(0.3198) H13C(0.2668) H14(0.1799) H17(0.3832) H18(0.5268)
 H19(0.6213) H20(0.573) H21(0.4315) H25(0.3072) H26(0.2726) H27(0.2011)
 H28(0.1674) H29(0.2028) H34A(0.3089) H34B(0.3911) H35A(0.4186) H35B(0.3269)
 H36(0.5483) H37(0.5599) H38(0.4812) H39(0.3944) H40A(0.2095) H40B(0.2124)
 H40C(0.2041) H42A(0.4475) H42B(0.5418) H42C(0.5242) H43(0.6093) H46(0.6761)
 H47(0.722) H48(0.7853) H49(0.8019) H50(0.7544) H54(0.9473) H55(1.0425)
 H56(1.0153) H57(0.8916) H58(0.7954)
;