Synthesis of 2(1H)-Pyrazinone Phosphonates via an Arbuzov-type Reaction
Jo Alen; Liliana Dobrzańska; Wim M. De Borggraeve; Frans Compernolle; Journal of Organic Chemistry 72 (2007) 1055–1057; doi:10.1021/jo062176a

data_4022690
_publ_section_title
;
 Synthesis of 2(1H)-Pyrazinone Phosphonates via an Arbuzov-type Reaction
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1055
_journal_page_last               1057
_journal_paper_doi               10.1021/jo062176a
_journal_volume                  72
_journal_year                    2007
_chemical_formula_moiety         'C7 H6 Cl2 N2 O'
_chemical_formula_sum            'C7 H6 Cl2 N2 O'
_chemical_formula_weight         205.04
_chemical_name_common            try
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.0839(17)
_cell_length_b                   13.697(3)
_cell_length_c                   7.4042(16)
_cell_measurement_temperature    100(2)
_cell_volume                     819.8(3)
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'X-Seed (Barbour 2001)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.954
_diffrn_measurement_device_type  'Bruker APEX CCD area-detector'
_diffrn_measurement_method       \w
_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  0.0648
_diffrn_reflns_av_sigmaI/netI    0.0576
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            4802
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         28.25
_diffrn_reflns_theta_min         2.93
_exptl_absorpt_coefficient_mu    0.738
_exptl_absorpt_correction_T_max  0.9433
_exptl_absorpt_correction_T_min  0.8725
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1997)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.661
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.455
_refine_diff_density_min         -0.465
_refine_diff_density_rms         0.103
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.07(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.213
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     109
_refine_ls_number_reflns         1045
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.211
_refine_ls_R_factor_all          0.0667
_refine_ls_R_factor_gt           0.0586
_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^)+(0.0459P)^2^+0.3562P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1066
_refine_ls_wR_factor_ref         0.1094
_reflns_number_gt                954
_reflns_number_total             1045
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo062176asi20061019_105156.cif
_cod_data_source_block           I
_cod_database_code               4022690