Structures of the Intermediates Formed in the Ring-Opening Reaction of 2-Chloro-3-nitropyridine
LeRoy W. Haynes; Virginia B. Pett; Journal of Organic Chemistry 72 (2007) 633–635; doi:10.1021/jo062003l

data_4022651
_publ_contact_author_address
;The College of Wooster
Department of Chemistry
943 College Mall
Wooster, OH 44691
;
_publ_contact_author_email       haynes@wooster.edu
_publ_contact_author_fax         330-263-2386
_publ_contact_author_name        'LeRoy W. Haynes'
_publ_contact_author_phone       330-263-2012
_publ_section_title
;
 Structures of the Intermediates Formed in the Ring-Opening
 Reaction of 2-Chloro-3-nitropyridine
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              633
_journal_page_last               635
_journal_paper_doi               10.1021/jo062003l
_journal_volume                  72
_journal_year                    2007
_chemical_compound_source
;
Isolated by Reinheimer et al. from the reaction of 
2-chloro-3-nitropyridine and two equivalents of 
hydroxide
;
_chemical_formula_moiety         'Na 1+, C5 H3 N2 O3 1-, H2 O1'
_chemical_formula_sum            'C5 H5 N2 Na O4'
_chemical_formula_weight         180.10
_chemical_name_systematic
'3-pentenenitrile, 2-nitro-5-oxo-, ion(-1), sodium'
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                109.196(4)
_cell_angle_beta                 98.770(4)
_cell_angle_gamma                95.216(4)
_cell_formula_units_Z            2
_cell_length_a                   3.5647(8)
_cell_length_b                   10.192(2)
_cell_length_c                   10.679(2)
_cell_measurement_reflns_used    1846
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      28.28
_cell_measurement_theta_min      2.40
_cell_volume                     357.98(14)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection
;
Bruker SMART; SADABS V.2.03
(Bruker, 2001)
;
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_pressure         100
_diffrn_ambient_temperature      93(2)
_diffrn_measured_fraction_theta_full 0.965
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0303
_diffrn_reflns_av_sigmaI/netI    0.0533
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            3150
_diffrn_reflns_theta_full        28.32
_diffrn_reflns_theta_max         28.32
_diffrn_reflns_theta_min         2.06
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'Bruker SMART area detector diffractometer'
_diffrn_standards_decay_%        -0.38
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.193
_exptl_absorpt_correction_T_max  0.970297
_exptl_absorpt_correction_T_min  0.678739
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS V.2.03
(Bruker, 2001)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.671
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             184
_exptl_crystal_recrystallization_method
'Vapor diffusion of petroleum ether into acetone solution of compound'
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.351
_refine_diff_density_min         -0.351
_refine_diff_density_rms         0.079
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     124
_refine_ls_number_reflns         1726
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0800
_refine_ls_R_factor_gt           0.0528
_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^)+(0.0703P)^2^+0.1324P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1243
_refine_ls_wR_factor_ref         0.1357
_reflns_number_gt                1263
_reflns_number_total             1726
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo062003lsi20060928_034007.cif
_cod_data_source_block           vbp01m
_cod_database_code               4022651