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_4515124
_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_moiety         'C17 H19 N3 O3'
_chemical_formula_sum            'C17 H19 N3 O3'
_chemical_formula_weight         313.35
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-10-10
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_cell_angle_alpha                90
_cell_angle_beta                 90.699(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.4051(12)
_cell_length_b                   9.1919(11)
_cell_length_c                   18.885(2)
_cell_measurement_reflns_used    3475
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      26.619
_cell_measurement_theta_min      2.465
_cell_volume                     1632.5(3)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       '/w scan'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0207
_diffrn_reflns_av_unetI/netI     0.0240
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            9566
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.611
_diffrn_reflns_theta_min         3.076
_diffrn_standards_decay_%        1
_diffrn_standards_interval_count 60
_diffrn_standards_number         1
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6833
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/3 (Bruker,2014/3) was used for absorption correction.
wR2(int) was 0.0627 before and 0.0319 after correction.
The Ratio of minimum to maximum transmission is 0.9164.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_description       block
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.257
_refine_diff_density_min         -0.309
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       0.018(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     231
_refine_ls_number_reflns         3691
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0798
_refine_ls_R_factor_gt           0.0530
_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^)+(0.0724P)^2^+0.5095P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1405
_refine_ls_wR_factor_ref         0.1623
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2568
_reflns_number_total             3691
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ao8b03284_si_002.cif
_cod_data_source_block           ysjzqx10_0m
_cod_database_code               4515124
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Sof(O1A)=Sof(O2A)=1-FVAR(1)
 Sof(O1)=Sof(O2)=FVAR(1)
3.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B)
3.b Aromatic/amide H refined with riding coordinates:
 N3(H3), C3(H3A), C12(H12), C13(H13), C15(H15), C16(H16)
3.c Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C8(H8A,H8B,H8C), C17(H17A,H17B,H17C)
;
_shelx_res_checksum              1509
_shelx_hkl_checksum              36981
_shelx_shelxl_version_number     2016/6
_olex2_submission_special_instructions 'No special instructions were received'