Three-Component Cascade Reaction of 1,1-Enediamines, <i>N</i>,<i>N</i>-Dimethylformamide Dimethyl Acetal, and 1,3-Dicarbonyl Compounds: Selective Synthesis of Diverse 2-Aminopyridine Derivatives.
Zi, Quan-Xing; Yan, Sheng-Jiao; Yang, Chang-Long; Li, Kun; Lin, Jun; ACS omega 4 (2019) 2863–2873; doi:10.1021/acsomega.8b03284

data_4515125
_publ_section_title
;
 Three-Component Cascade Reaction of 1,1-Enediamines,
 <i>N</i>,<i>N</i>-Dimethylformamide Dimethyl Acetal, and 1,3-Dicarbonyl
 Compounds: Selective Synthesis of Diverse 2-Aminopyridine Derivatives.
;
_journal_issue                   2
_journal_name_full               'ACS omega'
_journal_page_first              2863
_journal_page_last               2873
_journal_paper_doi               10.1021/acsomega.8b03284
_journal_volume                  4
_journal_year                    2019
_chemical_formula_sum            'C18 H18 Cl N3 O3'
_chemical_formula_weight         359.80
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.2644(9)
_cell_length_b                   9.8335(14)
_cell_length_c                   27.698(4)
_cell_measurement_reflns_used    1953
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      20.3624
_cell_measurement_theta_min      2.5403
_cell_volume                     1706.2(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0410
_diffrn_reflns_av_unetI/netI     0.0452
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            9621
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         1.470
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.247
_exptl_absorpt_correction_T_max  0.948
_exptl_absorpt_correction_T_min  0.930
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_description       block
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.270
_exptl_crystal_size_min          0.220
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details
;
 Flack x determined using 748 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.58(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         2990
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0553
_refine_ls_R_factor_gt           0.0369
_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^)+(0.0359P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0747
_refine_ls_wR_factor_ref         0.0827
_reflns_Friedel_coverage         0.692
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.994
_reflns_number_gt                2272
_reflns_number_total             2990
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ao8b03284_si_003.cif
_cod_data_source_block           1
_cod_original_cell_volume        1706.3(4)
_cod_database_code               4515125
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.930
_shelx_estimated_absorpt_t_max   0.948
_shelx_res_checksum              80072
_shelx_hkl_checksum              91874