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_7214127
_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         'C28 H31 Cl N2 O'
_chemical_formula_sum            'C28 H31 Cl N2 O'
_chemical_formula_weight         447.00
_chemical_name_systematic
; 
 (Z)-3-[(2-amino-4,5-dimethylphenyl)amino]-4-
 (4-tert-butylphenyl)-1-(4-chlorophenyl)but-2-en-1-one
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 92.354(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.7713(9)
_cell_length_b                   16.573(2)
_cell_length_c                   25.145(4)
_cell_measurement_reflns_used    6787
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      67.739
_cell_measurement_theta_min      3.152
_cell_volume                     2403.0(6)
_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 0.975
_diffrn_measured_fraction_theta_max 0.975
_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  0.0744
_diffrn_reflns_av_sigmaI/netI    0.0493
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            26321
_diffrn_reflns_theta_full        67.58
_diffrn_reflns_theta_max         67.58
_diffrn_reflns_theta_min         3.19
_exptl_absorpt_coefficient_mu    1.569
_exptl_absorpt_correction_T_max  0.9090
_exptl_absorpt_correction_T_min  0.6159
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2010)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.236
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'transparent needle'
_exptl_crystal_F_000             952
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.195
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     294
_refine_ls_number_reflns         4215
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0753
_refine_ls_R_factor_gt           0.0403
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0470P)^2^+0.4186P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0874
_refine_ls_wR_factor_ref         0.0997
_reflns_number_gt                2948
_reflns_number_total             4215
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3gc41898g.txt
_cod_data_source_block           demb30
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/automatic-downloads/current/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7214127