Metal-free synthesis of substituted pyridines from aldehydes and NH4OAc under air
Yan, Rulong; Zhou, Xiaoqiang; Li, Ming; Li, Xiaoni; Kang, Xing; Liu, Xingxing; Huo, Xing; Huang, Guosheng; RSC Adv. 4 (2014) 50369–; doi:10.1039/C4RA10880A

data_7218413
_publ_section_title
;
 Metal-free synthesis of substituted pyridines from aldehydes and NH4OAc
 under air
;
_journal_issue                   92
_journal_name_full               'RSC Adv.'
_journal_page_first              50369
_journal_paper_doi               10.1039/C4RA10880A
_journal_volume                  4
_journal_year                    2014
_chemical_formula_moiety         'C17 H13 N'
_chemical_formula_sum            'C17 H13 N'
_chemical_formula_weight         231.28
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-06-07
_audit_creation_method
;
  Olex2 1.2
  (compiled Apr 23 2013 17:54:37, GUI svn.r4466)
;
_cell_angle_alpha                78.153(13)
_cell_angle_beta                 76.412(16)
_cell_angle_gamma                90.060(14)
_cell_formula_units_Z            2
_cell_length_a                   6.5135(13)
_cell_length_b                   7.3675(10)
_cell_length_c                   13.814(2)
_cell_measurement_reflns_used    891
_cell_measurement_temperature    297.1(3)
_cell_measurement_theta_max      26.4580
_cell_measurement_theta_min      3.8830
_cell_volume                     629.78(19)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'SUPERFLIP, J. Appl. Cryst. (2007) 40, 786-790'
_diffrn_ambient_temperature      297.1(3)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega  -20.00   26.50   1.5000   14.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.3700  -99.0000  -90.0000 31

  2 omega  -43.00   24.50   1.5000   14.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.3700   77.0000   60.0000 45

  3 omega    4.00   76.00   1.5000   14.0000
omega____ theta____ kappa____ phi______ frames
    -       22.8075   57.0000   30.0000 48

  4 omega  -49.00   56.00   1.5000   14.0000
omega____ theta____ kappa____ phi______ frames
    -       22.8075  -38.0000  120.0000 70

  5 omega    9.00   61.50   1.5000   14.0000
omega____ theta____ kappa____ phi______ frames
    -       22.8075  -99.0000  150.0000 35

  6 omega   -4.00   98.00   1.5000   14.0000
omega____ theta____ kappa____ phi______ frames
    -       22.8075   38.0000  -60.0000 68
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0981834000
_diffrn_orient_matrix_UB_12      -0.0368101000
_diffrn_orient_matrix_UB_13      0.0056598000
_diffrn_orient_matrix_UB_21      0.0537154000
_diffrn_orient_matrix_UB_22      0.0689797000
_diffrn_orient_matrix_UB_23      -0.0422280000
_diffrn_orient_matrix_UB_31      0.0078628000
_diffrn_orient_matrix_UB_32      0.0598217000
_diffrn_orient_matrix_UB_33      0.0332254000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_unetI/netI     0.0624
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            4324
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.68
_diffrn_reflns_theta_min         3.22
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.42724
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.220
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             244
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.267
_refine_diff_density_min         -0.314
_refine_diff_density_rms         0.076
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         4324
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.1594
_refine_ls_R_factor_gt           0.0948
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1916P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2805
_refine_ls_wR_factor_ref         0.3187
_reflns_number_gt                2148
_reflns_number_total             4324
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ra10880a2.cif
_cod_data_source_block           yangrl0605_twin1_hklf4
_cod_original_cell_volume        629.80(19)
_cod_database_code               7218413
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C10(H10), C11(H11), C13(H13),
 C14(H14), C15(H15), C16(H16), C17(H17)
;