Regioselective “hydroamination” of alk-3-ynones with non-symmetrical o-phenylenediamines. Synthesis of diversely substituted 3H-1,5-benzodiazepines via (Z)-3-amino-2-alkenones
Young, Jonathon; Schäfer, Christian; Solan, Agnes; Baldrica, Anthony; Belcher, Miranda; Nişanci, Bilal; Wheeler, Kraig A.; R. Trivedi, Evan; Török, Béla; Dembinski, Roman; RSC Adv. 6 (2016) 107081–; doi:10.1039/C6RA24291J

data_7227088
_publ_section_title
;
 Regioselective &#x201C;hydroamination&#x201D; of alk-3-ynones with
 non-symmetrical o-phenylenediamines. Synthesis of diversely substituted
 3H-1,5-benzodiazepines via (Z)-3-amino-2-alkenones
;
_journal_issue                   108
_journal_name_full               'RSC Adv.'
_journal_page_first              107081
_journal_paper_doi               10.1039/C6RA24291J
_journal_volume                  6
_journal_year                    2016
_chemical_formula_moiety         'C23 H19 N3 O2'
_chemical_formula_sum            'C23 H19 N3 O2'
_chemical_formula_weight         369.41
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2016-10-05 deposited with the CCDC.
2016-10-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   21.4737(10)
_cell_length_b                   16.0302(8)
_cell_length_c                   5.5546(3)
_cell_measurement_reflns_used    4714
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      67.609
_cell_measurement_theta_min      3.440
_cell_volume                     1912.05(17)
_computing_cell_refinement       APEX2
_computing_data_collection       'APEX2 (Bruker, 2013)'
_computing_data_reduction
;
TWINABS (Bruker, 2012) and XPREP (Bruker, 2013)
;
_computing_molecular_graphics    'XSEED (Barbour, 2001)'
_computing_publication_material  'XSEED (Barbour, 2001)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.1073
_diffrn_reflns_av_unetI/netI     0.0545
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            28119
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.220
_diffrn_reflns_theta_min         3.440
_exptl_absorpt_coefficient_mu    0.668
_exptl_absorpt_correction_T_max  0.753
_exptl_absorpt_correction_T_min  0.670
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2014/5, Bruker AXS'
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_description       'transparent rod'
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.449
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.091
_refine_diff_density_max         0.141
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details
;
 Flack x determined using 881 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.2(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.997
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         3485
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.997
_refine_ls_R_factor_all          0.0760
_refine_ls_R_factor_gt           0.0472
_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^)+(0.0630P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1067
_refine_ls_wR_factor_ref         0.1208
_reflns_Friedel_coverage         0.786
_reflns_Friedel_fraction_full    0.986
_reflns_Friedel_fraction_max     0.984
_reflns_number_gt                2506
_reflns_number_total             3485
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6ra24291j2.cif
_cod_data_source_block           demb33
_cod_database_code               7227088
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.753
_shelx_estimated_absorpt_t_max   0.942
_shelx_res_checksum              4102