Catalyst-free chemo-/regio-/stereo-selective amination of alk-3-ynones. Synthesis of 1,5-benzodiazepines and 3-amino-2-alkenones
Solan, Agnes; Nişanci, Bilal; Belcher, Miranda; Young, Jonathon; Schäfer, Christian; Wheeler, Kraig A.; Török, Béla; Dembinski, Roman; Green Chemistry 16 (2014) 1120–; doi:10.1039/c3gc41898g

data_7214126
_publ_section_title
;
 Catalyst-free chemo-/regio-/stereo-selective amination of alk-3-ynones.
 Synthesis of 1,5-benzodiazepines and 3-amino-2-alkenones
;
_journal_issue                   3
_journal_name_full               'Green Chemistry'
_journal_page_first              1120
_journal_paper_doi               10.1039/c3gc41898g
_journal_volume                  16
_journal_year                    2014
_chemical_formula_moiety         'C23 H20 N2'
_chemical_formula_sum            'C23 H20 N2'
_chemical_formula_weight         324.41
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.2819(9)
_cell_length_b                   10.7707(9)
_cell_length_c                   15.6284(14)
_cell_measurement_reflns_used    6015
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      66.564
_cell_measurement_theta_min      4.104
_cell_volume                     1730.7(3)
_computing_cell_refinement       APEX2
_computing_data_collection       'APEX2 (Bruker, 2010)'
_computing_data_reduction
;
SAINT (Bruker, 2008) and XPREP (Bruker, 2008)
;
_computing_molecular_graphics    'XSEED (Barbour, 2001)'
_computing_publication_material  'XSEED (Barbour, 2001)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0470
_diffrn_reflns_av_sigmaI/netI    0.0232
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            28483
_diffrn_reflns_theta_full        67.79
_diffrn_reflns_theta_max         67.79
_diffrn_reflns_theta_min         4.99
_exptl_absorpt_coefficient_mu    0.561
_exptl_absorpt_correction_T_max  0.841
_exptl_absorpt_correction_T_min  0.640
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2010)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.245
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'transparent needle'
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.346
_exptl_crystal_size_mid          0.192
_exptl_crystal_size_min          0.134
_refine_diff_density_max         0.944
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.056
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.2(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3134
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0568
_refine_ls_R_factor_gt           0.0521
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0907P)^2^+0.8657P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1401
_refine_ls_wR_factor_ref         0.1445
_reflns_number_gt                2901
_reflns_number_total             3134
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3gc41898g.txt
_cod_data_source_block           demb25
_cod_database_code               7214126