Novel and Facile Synthesis of 1-Benzazepines via Copper-Catalyzed Oxidative C(sp3)-H/C(sp2)-H Cross-Coupling
Wang, Rui; Jin, Ruoxing; Qin, Zi-Yang; Bian, Kang-Jie; Wang, Xi-Sheng; Chem. Commun.  (2017) –; doi:10.1039/C7CC07027F

data_7120814
_publ_section_title
;
 Novel and Facile Synthesis of 1-Benzazepines via Copper-Catalyzed
 Oxidative C(sp3)-H/C(sp2)-H Cross-Coupling
;
_journal_name_full               'Chem. Commun.'
_journal_paper_doi               10.1039/C7CC07027F
_journal_year                    2017
_chemical_formula_sum            'C33 H33 N'
_chemical_formula_weight         443.60
_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   mixed
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2017-07-14 deposited with the CCDC.
2017-10-24 downloaded from the CCDC.
;
_cell_angle_alpha                92.791(3)
_cell_angle_beta                 97.221(2)
_cell_angle_gamma                94.987(2)
_cell_formula_units_Z            2
_cell_length_a                   8.9337(2)
_cell_length_b                   10.9430(4)
_cell_length_c                   13.0698(4)
_cell_measurement_reflns_used    5138
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      71.0740
_cell_measurement_theta_min      5.4520
_cell_volume                     1260.49(7)
_computing_cell_refinement       'CrysAlisPro (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro (Rigaku OD, 2015)'
_computing_molecular_graphics    'Ortep-3 (L. J. Farrugia, 2001)'
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      291(2)
_diffrn_detector_area_resol_mean 5.2169
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0195
_diffrn_reflns_av_unetI/netI     0.0263
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8360
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.234
_diffrn_reflns_theta_min         3.415
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.502
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85898
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.169
_exptl_crystal_description       block
_exptl_crystal_F_000             476
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.210
_refine_diff_density_max         0.510
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       0.0089(8)
_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   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     316
_refine_ls_number_reflns         4740
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0529
_refine_ls_R_factor_gt           0.0473
_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^)+(0.0684P)^2^+0.2744P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1308
_refine_ls_wR_factor_ref         0.1369
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4125
_reflns_number_total             4740
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7cc07027f2.cif
_cod_data_source_block           shelxl
_cod_database_code               7120814
_shelx_estimated_absorpt_t_min   0.889
_shelx_estimated_absorpt_t_max   0.902
_shelxl_version_number           2013-4
_shelx_res_checksum              31951
_shelx_hkl_checksum              33654