Synthesis of 2-Aza-1,3-butadienes through Gold-Catalyzed Intermolecular Ynamide Amination/C-H Functionalization.
Shu, Chao; Shen, Cang-Hai; Wang, Yong-Heng; Li, Long; Li, Tao; Lu, Xin; Ye, Long-Wu; Organic letters  (2016) –; doi:10.1021/acs.orglett.6b02267

data_1544026
_publ_section_title
;
 Synthesis of 2-Aza-1,3-butadienes through Gold-Catalyzed Intermolecular
 Ynamide Amination/C-H Functionalization.
;
_journal_name_full               'Organic letters'
_journal_paper_doi               10.1021/acs.orglett.6b02267
_journal_year                    2016
_chemical_formula_moiety         'C22 H19 Br N2 O2 S'
_chemical_formula_sum            'C22 H19 Br N2 O2 S'
_chemical_formula_weight         455.36
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2016-06-19
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.06 svn.r3119 for OlexSys, GUI svn.r4979)
;
_cell_angle_alpha                90
_cell_angle_beta                 115.135(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.662(3)
_cell_length_b                   7.774(2)
_cell_length_c                   12.367(3)
_cell_measurement_reflns_used    4250
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      26.87
_cell_measurement_theta_min      3.16
_cell_volume                     1015.0(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      273.15
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0272
_diffrn_reflns_av_unetI/netI     0.0547
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7655
_diffrn_reflns_point_group_measured_fraction_full 0.966
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.994
_diffrn_reflns_theta_min         1.819
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    2.148
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.490
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.582
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details
;
 Flack x determined using 1364 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.040(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.986
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3854
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.986
_refine_ls_R_factor_all          0.0398
_refine_ls_R_factor_gt           0.0343
_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^)+(0.0301P)^2^]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0771
_refine_ls_wR_factor_ref         0.0783
_reflns_Friedel_coverage         0.803
_reflns_Friedel_fraction_full    0.937
_reflns_Friedel_fraction_max     0.933
_reflns_number_gt                3394
_reflns_number_total             3854
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b02267_si_002.cif
_cod_data_source_block           ye1107m
_cod_original_cell_volume        1015.1(5)
_cod_database_code               1544026
_shelxl_version_number           2013-2
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Me refined with riding coordinates:
 C101(H10A,H10B,H10C)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C3(H3), C12(H12), C13(H13), C15(H15), C16(H16), C32(H32), C33(H33),
 C34(H34), C35(H35), C36(H36), C42(H42), C43(H43), C44(H44), C45(H45), C46(H46)
;
_shelx_res_checksum              43066
_shelx_hkl_checksum              67870
_olex2_submission_special_instructions 'No special instructions were received'