Intramolecular Arylation of Tertiary Enamides through Pd(OAc)<sub>2</sub>-Catalyzed Dehydrogenative Cross-Coupling Reaction: Construction of Fused N-Heterocyclic Scaffolds and Synthesis of Isoindolobenzazepine Alkaloids.
Zhu, Wenju; Tong, Shuo; Zhu, Jieping; Wang, Mei-Xiang; The Journal of organic chemistry 84 (2019) 2870–2878; doi:10.1021/acs.joc.9b00010

data_4033695
_publ_section_title
;
 Intramolecular Arylation of Tertiary Enamides through
 Pd(OAc)<sub>2</sub>-Catalyzed Dehydrogenative Cross-Coupling Reaction:
 Construction of Fused N-Heterocyclic Scaffolds and Synthesis of
 Isoindolobenzazepine Alkaloids.
;
_journal_issue                   5
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              2870
_journal_page_last               2878
_journal_paper_doi               10.1021/acs.joc.9b00010
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C21 H21 N O7'
_chemical_formula_sum            'C21 H21 N O7'
_chemical_formula_weight         399.39
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2015-07-09
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                90
_cell_angle_beta                 100.924(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.5519(16)
_cell_length_b                   13.646(3)
_cell_length_c                   15.984(3)
_cell_measurement_reflns_used    6549
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4795
_cell_measurement_theta_min      1.2975
_cell_volume                     1831.5(6)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'CIFTAB (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2014)'
_computing_structure_solution
;
'SHELXT (Sheldrick, 2014)'
;
_diffrn_ambient_temperature      173.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
scan:
	Number of images: 360
	           Slice: -110.0000 - 70.0000
	     Image width: 0.5000
	        Exp time: 3.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 180.0000
	             XTD: 40.0243
	          2theta: -19.9839
scan:
	Number of images: 360
	           Slice: -110.0000 - 70.0000
	     Image width: 0.5000
	        Exp time: 3.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 0.0000
	             XTD: 40.0243
	          2theta: -19.9839
scan:
	Number of images: 344
	           Slice: -110.0000 - 62.0000
	     Image width: 0.5000
	        Exp time: 3.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 90.0000
	             XTD: 40.0243
	          2theta: -19.9839
;
_diffrn_measurement_device
;
Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_device_details
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'MM007-HF CCD(Saturn 724+)'
_diffrn_measurement_method       '\w scans at fixed \c = 45\%'
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      0.0299
_diffrn_orient_matrix_UB_12      -0.0820
_diffrn_orient_matrix_UB_13      -0.0810
_diffrn_orient_matrix_UB_21      0.0621
_diffrn_orient_matrix_UB_22      0.0364
_diffrn_orient_matrix_UB_23      -0.0139
_diffrn_orient_matrix_UB_31      0.0324
_diffrn_orient_matrix_UB_32      -0.0414
_diffrn_orient_matrix_UB_33      0.0361
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0419
_diffrn_reflns_av_unetI/netI     0.0236
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            23539
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.479
_diffrn_reflns_theta_min         1.978
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0000
_diffrn_source_power             1.2000
_diffrn_source_voltage           50.0000
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7959
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.448
_exptl_crystal_description       block
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.311
_refine_diff_density_min         -0.176
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.162
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     270
_refine_ls_number_reflns         4191
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.162
_refine_ls_R_factor_all          0.0521
_refine_ls_R_factor_gt           0.0502
_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^)+(0.0495P)^2^+0.7996P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1190
_refine_ls_wR_factor_ref         0.1203
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4076
_reflns_number_total             4191
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b00010_si_002.cif
_cod_data_source_block           mx3941
_cod_database_code               4033695
_diffrn_number_total             4379
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C15(H15A,H15B)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C16(H16), C19(H19)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C2(H2A,H2B,H2C), C20(H20A,H20B,H20C), C21(H21A,H21B,H21C)
;
_shelx_res_checksum              16535
_shelx_hkl_checksum              67008
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'