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_4515126
_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         'C21 H17 N3 O3'
_chemical_formula_sum            'C21 H17 N3 O3'
_chemical_formula_weight         359.38
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_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                 104.230(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   26.9468(5)
_cell_length_b                   5.1107(9)
_cell_length_c                   26.9471(5)
_cell_measurement_reflns_used    2058
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      20.63
_cell_measurement_theta_min      2.46
_cell_volume                     3597.2(7)
_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 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.935
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0719
_diffrn_reflns_av_unetI/netI     0.1001
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.935
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            21474
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.935
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.020
_diffrn_reflns_theta_min         0.780
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6668
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/3 (Bruker,2014/3) was used for absorption correction.
wR2(int) was 0.0656 before and 0.0381 after correction.
The Ratio of minimum to maximum transmission is 0.8943.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_description       block
_exptl_crystal_F_000             1504
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.197
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       0.0024(4)
_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   0.962
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     491
_refine_ls_number_reflns         7830
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.962
_refine_ls_R_factor_all          0.1615
_refine_ls_R_factor_gt           0.0576
_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^)+(0.0465P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0981
_refine_ls_wR_factor_ref         0.1285
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3605
_reflns_number_total             7830
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ao8b03284_si_004.cif
_cod_data_source_block           ysjzqx7_0m
_cod_database_code               4515126
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.6465(12) 0.3535(12)
2. 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
3.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C14(H14A,H14B), C34(H34A,H34B), C35(H35A,H35B)
3.b Aromatic/amide H refined with riding coordinates:
 N3(H3), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12), C16(H16), C17(H17),
 C19(H19), C20(H20), N6(H6), C29(H29), C30(H30), C31(H31), C32(H32), C33(H33),
 C37(H37), C38(H38), C40(H40), C41(H41)
3.c Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C42(H42A,H42B,H42C)
;
_shelx_res_checksum              42970
_shelx_hkl_checksum              75147
_shelx_shelxl_version_number     2016/6
_olex2_submission_special_instructions 'No special instructions were received'