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_4031106
_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         'C17 H21 N O'
_chemical_formula_sum            'C17 H21 N O'
_chemical_formula_weight         255.35
_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
_audit_creation_date             2014-02-08
_audit_creation_method
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Olex2 1.2
(compiled 2013.12.10 svn.r2853 for OlexSys, GUI svn.r4736)
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_cell_angle_alpha                90
_cell_angle_beta                 93.678(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.6641(3)
_cell_length_b                   17.3063(8)
_cell_length_c                   10.5169(4)
_cell_measurement_reflns_used    5348
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      75.8980
_cell_measurement_theta_min      4.8540
_cell_volume                     1392.06(10)
_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
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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)
;
_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)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4839
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_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      -0.0771788000
_diffrn_orient_matrix_UB_12      -0.0203140000
_diffrn_orient_matrix_UB_13      0.1275192000
_diffrn_orient_matrix_UB_21      0.1828077000
_diffrn_orient_matrix_UB_22      -0.0242942000
_diffrn_orient_matrix_UB_23      0.0552699000
_diffrn_orient_matrix_UB_31      0.0347453000
_diffrn_orient_matrix_UB_32      0.0831583000
_diffrn_orient_matrix_UB_33      0.0473524000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0491
_diffrn_reflns_av_unetI/netI     0.0320
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            14625
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.503
_diffrn_reflns_theta_min         4.928
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.580
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_correction_T_min  0.964
_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            colourless
_exptl_crystal_density_diffrn    1.218
_exptl_crystal_description       plate
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.2656
_exptl_crystal_size_mid          0.1603
_exptl_crystal_size_min          0.062
_refine_diff_density_max         0.160
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         2846
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0576
_refine_ls_R_factor_gt           0.0426
_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^)+(0.0497P)^2^+0.3941P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0983
_refine_ls_wR_factor_ref         0.1069
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2288
_reflns_number_total             2846
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo5b00670_si_003.cif
_cod_data_source_block           evde_ugent006
_cod_depositor_comments
'Adding full bibliography for 4031105--4031108.cif.'
_cod_database_code               4031106
_shelxl_version_number           2013-4
_chemical_oxdiff_formula         'C10 H10 N4 O4'
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H5A(0.027) H5B(0.027) H6A(0.026) H6B(0.026) H7(0.027) H8(0.03)
 H9(0.031) H10(0.029) H11(0.026) H12A(0.04) H12B(0.04) H12C(0.04) H13A(0.04)
 H13B(0.04) H13C(0.04) H15A(0.039) H15B(0.039) H15C(0.039) H16(0.028)
 H17A(0.034) H17B(0.034)
 Fixed X: H5A(0.3173) H5B(0.126) H6A(0.003) H6B(0.1666) H7(0.0038) H8(0.1322)
 H9(0.2917) H10(0.319) H11(0.4013) H12A(0.4626) H12B(0.6039) H12C(0.5357)
 H13A(0.2065) H13B(0.4017) H13C(0.2611) H15A(-0.3246) H15B(-0.2979) H15C(-
 0.1429) H16(-0.2578) H17A(-0.5182) H17B(-0.5436)
 Fixed Y: H5A(0.595) H5B(0.5824) H6A(0.6637) H6B(0.708) H7(0.4348) H8(0.3249)
 H9(0.3338) H10(0.4525) H11(0.7177) H12A(0.7214) H12B(0.743) H12C(0.6559)
 H13A(0.8215) H13B(0.8448) H13C(0.8246) H15A(0.6813) H15B(0.6352) H15C(0.6874)
 H16(0.484) H17A(0.5684) H17B(0.4868)
 Fixed Z: H5A(0.9919) H5B(1.0397) H6A(0.8858) H6B(0.9538) H7(0.6226)
 H8(0.7147) H9(0.9123) H10(1.0153) H11(0.6749) H12A(0.9457) H12B(0.8458)
 H12C(0.8558) H13A(0.6982) H13B(0.7465) H13C(0.8476) H15A(0.6289) H15B(0.4997)
 H15C(0.5626) H16(0.7407) H17A(0.6047) H17B(0.6819)
;
_shelx_res_checksum              40876
_shelx_hkl_checksum              42696