[5C + 1N] Annulation of 2,4-pentadienenitriles with hydroxylamine: a synthetic route to multi-substituted 2-aminopyridines.
Xin, Xiaoqing; Huang, Peng; Xiang, Dexuan; Zhang, Rui; Zhao, Fengyu; Zhang, Ning; Dong, Dewen; Organic & biomolecular chemistry 11 (2013) 1001–1006; doi:10.1039/c2ob27053f

data_7152799
_publ_section_title
;
 [5C + 1N] Annulation of 2,4-pentadienenitriles with hydroxylamine: a
 synthetic route to multi-substituted 2-aminopyridines.
;
_journal_issue                   6
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              1001
_journal_page_last               1006
_journal_paper_doi               10.1039/c2ob27053f
_journal_volume                  11
_journal_year                    2013
_chemical_formula_moiety         'C14 H13 N2 O2 Cl'
_chemical_formula_sum            'C14 H13 Cl N2 O2'
_chemical_formula_weight         276.72
_chemical_melting_point          ?
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 102.794(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   15.501(3)
_cell_length_b                   15.080(3)
_cell_length_c                   11.907(3)
_cell_measurement_reflns_used    6670
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      2.28
_cell_volume                     2714.2(10)
_computing_cell_refinement       'SMART(Bruker, 1998)'
_computing_data_collection       'SMART(Bruker, 1998)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Bruker, 1998)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0289
_diffrn_reflns_av_sigmaI/netI    0.0290
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            16791
_diffrn_reflns_theta_full        26.06
_diffrn_reflns_theta_max         26.06
_diffrn_reflns_theta_min         1.91
_exptl_absorpt_coefficient_mu    0.300
_exptl_absorpt_correction_T_max  0.760
_exptl_absorpt_correction_T_min  0.704
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   '(SADABS; Bruker, 1998)'
_exptl_crystal_colour            'light blue'
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             1083
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.160
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     343
_refine_ls_number_reflns         5331
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0858
_refine_ls_R_factor_gt           0.0537
_refine_ls_shift/su_max          0.012
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0662P)^2^+0.2773P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1249
_refine_ls_wR_factor_ref         0.1452
_reflns_number_gt                3440
_reflns_number_total             5331
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2ob27053f.txt
_cod_data_source_block           xq
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value 'not measured' was changed to '?' -
the value is undefined or not given.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'none' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_cell_volume        2714.3(10)
_cod_original_sg_symbol_Hall     -p2ybc
_cod_original_sg_symbol_H-M      P21/c
_cod_original_formula_sum        'C14 H13 N2 O2 Cl'
_cod_database_code               7152799