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_7227087
_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         'C18 H18 Cl N O'
_chemical_formula_sum            'C18 H18 Cl N O'
_chemical_formula_weight         299.78
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2016-05-01 deposited with the CCDC.
2016-10-24 downloaded from the CCDC.
;
_cell_angle_alpha                77.465(2)
_cell_angle_beta                 86.009(2)
_cell_angle_gamma                76.595(1)
_cell_formula_units_Z            2
_cell_length_a                   5.8282(2)
_cell_length_b                   10.3586(3)
_cell_length_c                   13.2061(4)
_cell_measurement_reflns_used    8132
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.202
_cell_measurement_theta_min      3.426
_cell_volume                     756.91(4)
_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 0.974
_diffrn_measured_fraction_theta_max 0.974
_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  0.0301
_diffrn_reflns_av_sigmaI/netI    0.0199
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            15426
_diffrn_reflns_theta_full        67.62
_diffrn_reflns_theta_max         67.62
_diffrn_reflns_theta_min         3.43
_exptl_absorpt_coefficient_mu    2.206
_exptl_absorpt_correction_T_max  0.7535
_exptl_absorpt_correction_T_min  0.4289
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2010)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'transparent plate'
_exptl_crystal_F_000             316
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.321
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         2658
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0316
_refine_ls_R_factor_gt           0.0301
_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^)+(0.0391P)^2^+0.3165P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0785
_refine_ls_wR_factor_ref         0.0798
_reflns_number_gt                2521
_reflns_number_total             2658
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6ra24291j2.cif
_cod_data_source_block           demb26
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/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 4268 2015-11-12 08:31:59Z antanas 
;
_cod_database_code               7227087