Synthesis of 2-aminopyridines via ruthenium-catalyzed [2+2+2] cycloaddition of 1,6- and 1,7-diynes with cyanamides: scope and limitations
Ye, Fei; Boukattaya, Fatma; Haddad, Mansour; Ratovelomanana-Vidal, Virginie; Michelet, Véronique; New Journal of Chemistry 42 (2018) 3222–; doi:10.1039/C7NJ04933A

data_7056967
_publ_section_title
;
 Synthesis of 2-aminopyridines via ruthenium-catalyzed [2+2+2]
 cycloaddition of 1,6- and 1,7-diynes with cyanamides: scope and
 limitations
;
_journal_issue                   5
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              3222
_journal_paper_doi               10.1039/C7NJ04933A
_journal_volume                  42
_journal_year                    2018
_chemical_formula_moiety         'C17 H21 Br N2 O5'
_chemical_formula_sum            'C17 H21 Br N2 O5'
_chemical_formula_weight         413.27
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_block_doi                 10.5517/ccdc.csd.cc1pbl2p
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2017-06-29 deposited with the CCDC.
2018-01-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 110.344(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   27.4912(7)
_cell_length_b                   11.5671(3)
_cell_length_c                   11.9907(3)
_cell_measurement_reflns_used    9929
_cell_measurement_temperature    200(1)
_cell_measurement_theta_max      30.49
_cell_measurement_theta_min      2.46
_cell_volume                     3575.12(16)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'SXGRAPH (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      200(1)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'curved graphite'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0160
_diffrn_reflns_av_unetI/netI     0.0157
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       39
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            21105
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.570
_diffrn_reflns_theta_min         1.930
_exptl_absorpt_coefficient_mu    2.330
_exptl_absorpt_correction_T_max  0.674
_exptl_absorpt_correction_T_min  0.401
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
R.H. Blessing, Acta Cryst. (1995), A51, 33-38
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.536
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1696
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.462
_refine_diff_density_min         -0.312
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         5484
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0308
_refine_ls_R_factor_gt           0.0236
_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^)+(0.0298P)^2^+2.8965P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0582
_refine_ls_wR_factor_ref         0.0611
_reflns_number_gt                4763
_reflns_number_total             5484
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7nj04933a2.cif
_cod_data_source_block           fy589
_cod_depositor_comments
'Adding full bibliography for 7056967--7056968.cif.'
_cod_database_code               7056967
_shelx_shelxl_version_number     2014/7
_shelx_res_checksum              32848