Diversity-oriented synthesis of dibenzoazocines and dibenzoazepines via a microwave-assisted intramolecular A(3)-coupling reaction.
Bariwal, Jitender B.; Ermolat'ev, Denis S.; Glasnov, Toma N.; Van Hecke, Kristof; Mehta, Vaibhav P.; Van Meervelt, Luc; Kappe, C. Oliver; Van der Eycken, Erik V.; Organic letters 12 (2010) 2774–2777; doi:10.1021/ol1008729

data_1503011
_publ_section_title
;
 Diversity-oriented synthesis of dibenzoazocines and dibenzoazepines via a
 microwave-assisted intramolecular A(3)-coupling reaction.
;
_journal_issue                   12
_journal_name_full               'Organic letters'
_journal_page_first              2774
_journal_page_last               2777
_journal_paper_doi               10.1021/ol1008729
_journal_volume                  12
_journal_year                    2010
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C25 H25 N O2 S'
_chemical_formula_sum            'C25 H25 N O2 S'
_chemical_formula_weight         403.53
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 100.916(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.3323(7)
_cell_length_b                   11.9758(10)
_cell_length_c                   10.5285(15)
_cell_measurement_temperature    100(2)
_cell_volume                     1031.59(19)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_publication_material  Platon
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'SMART 6000'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'crossed G\"obel mirrors'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0644
_diffrn_reflns_av_sigmaI/netI    0.0713
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            9209
_diffrn_reflns_theta_full        66.59
_diffrn_reflns_theta_max         66.59
_diffrn_reflns_theta_min         4.28
_exptl_absorpt_coefficient_mu    1.554
_exptl_absorpt_correction_T_max  0.856
_exptl_absorpt_correction_T_min  0.599
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             428
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.517
_refine_diff_density_min         -0.428
_refine_diff_density_rms         0.105
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.03(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.121
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     266
_refine_ls_number_reflns         3532
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.121
_refine_ls_R_factor_all          0.0669
_refine_ls_R_factor_gt           0.0554
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1123P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1325
_refine_ls_wR_factor_ref         0.1731
_reflns_number_gt                3174
_reflns_number_total             3532
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol1008729_si_003.cif
_cod_data_source_block           ev22
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               1503011