Intermolecular Oxidative Decarbonylative [2+2+2] Carbocyclization of N-(2-Ethynylaryl)acrylamides with Tertiary Alkyl Aldehydes involving C(sp3)-H Functionalization
Li, Yang; Pan, Gao-Hui; Hu, Ming; Liu, Bang; Song, Ren-Jie; Li, Jin-Heng; Chem. Sci.  (2016) –; doi:10.1039/C6SC02451C

data_1543723
_publ_section_title
;
 Intermolecular Oxidative Decarbonylative [2+2+2] Carbocyclization of
 N-(2-Ethynylaryl)acrylamides with Tertiary Alkyl Aldehydes involving
 C(sp3)-H Functionalization
;
_journal_name_full               'Chem. Sci.'
_journal_paper_doi               10.1039/C6SC02451C
_journal_year                    2016
_chemical_formula_moiety         'C23 H24 Br N O'
_chemical_formula_sum            'C23 H24 Br N O'
_chemical_formula_weight         410.34
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2015-11-24 deposited with the CCDC.
2016-07-21 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.8036(9)
_cell_length_b                   21.3495(16)
_cell_length_c                   7.9601(6)
_cell_measurement_reflns_used    4493
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.55
_cell_measurement_theta_min      1.91
_cell_volume                     2006.0(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0281
_diffrn_reflns_av_sigmaI/netI    0.0599
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            11717
_diffrn_reflns_theta_full        27.55
_diffrn_reflns_theta_max         27.55
_diffrn_reflns_theta_min         1.91
_exptl_absorpt_coefficient_mu    2.060
_exptl_absorpt_correction_T_max  0.7081
_exptl_absorpt_correction_T_min  0.6487
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SHELXL-97 (Sheldrick, 2008)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_density_meas      1.359
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       lump
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.157
_refine_diff_density_min         -0.307
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.003(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         4493
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.004
_refine_ls_R_factor_all          0.0496
_refine_ls_R_factor_gt           0.0318
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0056P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0656
_refine_ls_wR_factor_ref         0.0707
_reflns_number_gt                3486
_reflns_number_total             4493
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6sc02451c2.cif
_cod_data_source_block           ljh034
_cod_original_sg_symbol_Hall     P2c-2n
_cod_original_sg_symbol_H-M      Pna21
_cod_database_code               1543723