The dipolar cycloaddition of methyl acrylate to 1,5,6-trimethyl-3-oxidopyrazinium
Madeleine Helliwell; You Yun; John A. Joule; Acta Crystallographica Section E 62 (2006) o1293–o1294; doi:10.1107/S1600536806007501

data_2208642
_publ_section_title
;
 The dipolar cycloaddition of methyl acrylate to
 1,5,6-trimethyl-3-oxidopyrazinium
;
_journal_coeditor_code           JH2006
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1293
_journal_page_last               o1294
_journal_paper_doi               10.1107/S1600536806007501
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C11 H16 N2 O3'
_chemical_formula_moiety         'C11 H16 N2 O3'
_chemical_formula_sum            'C11 H16 N2 O3'
_chemical_formula_weight         224.26
_chemical_name_systematic
;
methyl
8-methyl-4-methylene-2-oxo-3,8-diazabicyclo[3.2.1]octane-6-exo-carboxylate
;
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 102.23(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.818(10)
_cell_length_b                   7.89(2)
_cell_length_c                   14.80(3)
_cell_measurement_reflns_used    17414
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.97
_cell_measurement_theta_min      2.12
_cell_volume                     1120(4)
_computing_cell_refinement       'DENZO (Otwinowski, 1988)'
_computing_data_collection
'MSC R-AXIS 11 Control (Molecular Structure Corporation, 1992)'
_computing_data_reduction        'DENZO (Otwinowski, 1988)'
_computing_molecular_graphics    'SHELXTL (Bruker, 2001)'
_computing_publication_material
'teXsan (Molecular Structure Corporation, 1995)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution
;
SAPI91 (Fan, 1991)
;
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.901
_diffrn_measured_fraction_theta_max 0.901
_diffrn_measurement_device       'Rigaku R-AXIS'
_diffrn_measurement_method       '116 \\times 3\% \f'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Rigaku rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.037
_diffrn_reflns_av_sigmaI/netI    0.0206
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            17414
_diffrn_reflns_theta_full        24.97
_diffrn_reflns_theta_max         24.97
_diffrn_reflns_theta_min         2.12
_diffrn_standards_decay_%        0.00
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.330
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.159
_refine_diff_density_min         -0.128
_refine_ls_extinction_coef       0.037(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         1767
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0384
_refine_ls_R_factor_gt           0.0313
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0555P)^2^+0.1608P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0847
_refine_ls_wR_factor_ref         0.0890
_reflns_number_gt                1516
_reflns_number_total             1767
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jh2006.cif
_cod_data_source_block           4
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2208642