Pd-Catalyzed Hydroamination of Alkoxyallenes with Azole Heterocycles: Examples and Mechanistic Proposal.
Bernar, Ivan; Fiser, Béla; Blanco-Ania, Daniel; Gómez-Bengoa, Enrique; Rutjes, Floris P. J. T.; Organic letters 19 (2017) 4211–4214; doi:10.1021/acs.orglett.7b01826

data_1547081
_publ_section_title
;
 Pd-Catalyzed Hydroamination of Alkoxyallenes with Azole Heterocycles:
 Examples and Mechanistic Proposal.
;
_journal_issue                   16
_journal_name_full               'Organic letters'
_journal_page_first              4211
_journal_page_last               4214
_journal_paper_doi               10.1021/acs.orglett.7b01826
_journal_volume                  19
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C17 H18 N4 O3'
_chemical_formula_sum            'C17 H18 N4 O3'
_chemical_formula_weight         326.35
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_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-2016/6
_cell_angle_alpha                113.149(2)
_cell_angle_beta                 92.819(2)
_cell_angle_gamma                112.907(2)
_cell_formula_units_Z            2
_cell_length_a                   8.8973(5)
_cell_length_b                   10.3854(6)
_cell_length_c                   10.5682(5)
_cell_measurement_reflns_used    9957
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      31.5
_cell_measurement_theta_min      2.4
_cell_volume                     803.17(8)
_computing_cell_refinement       Peakref
_computing_data_collection       Apex3
_computing_data_reduction        SAINT,SADABS-2014/5
_computing_molecular_graphics    'PLATON, Shelxle'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 10.4
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'Bruker D8 Quest Apex3'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_detector       Photon100
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0219
_diffrn_reflns_av_unetI/netI     0.0157
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            69117
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.605
_diffrn_reflns_theta_min         2.381
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  0.7462
_exptl_absorpt_correction_T_min  0.7219
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_description       plate
_exptl_crystal_F_000             344
_exptl_crystal_size_max          0.742
_exptl_crystal_size_mid          0.543
_exptl_crystal_size_min          0.076
_refine_diff_density_max         0.574
_refine_diff_density_min         -0.301
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details
;
 Flack x determined using 4575 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.16(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     437
_refine_ls_number_reflns         10730
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0476
_refine_ls_R_factor_gt           0.0429
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0781P)^2^+0.1336P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1156
_refine_ls_wR_factor_ref         0.1200
_reflns_Friedel_coverage         0.995
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.991
_reflns_number_gt                9906
_reflns_number_total             10730
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b01826_si_003.cif
_cod_data_source_block           p1670a
_cod_database_code               1547081
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_min   0.933
_shelx_estimated_absorpt_t_max   0.993
_shelx_res_checksum              72842
_shelx_hkl_checksum              84283