The dipolar cycloaddition of methyl acrylate to 5,6-diethyl-1-methyl-3-oxidopyrazinium
Madeleine Helliwell; Yun You; John A. Joule; Acta Crystallographica Section E 62 (2006) o2318–o2320; doi:10.1107/S1600536806017107

data_2209232
_publ_section_title
;
 The dipolar cycloaddition of methyl acrylate to
 5,6-diethyl-1-methyl-3-oxidopyrazinium
;
_journal_coeditor_code           KJ2003
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2318
_journal_page_last               o2320
_journal_paper_doi               10.1107/S1600536806017107
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C13 H20 N2 O3'
_chemical_formula_moiety         'C13 H20 N2 O3'
_chemical_formula_sum            'C13 H20 N2 O3'
_chemical_formula_weight         252.31
_chemical_name_systematic
;
methyl
(Z)-5-ethyl-4-ethylidene-8-methyl-2-oxo-3,8-diazabicyclo[3.2.1]octane-6-endo-
6-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                 90.36(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.00(2)
_cell_length_b                   8.842(10)
_cell_length_c                   14.693(10)
_cell_measurement_reflns_used    10171
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.00
_cell_measurement_theta_min      2.04
_cell_volume                     1299(3)
_computing_cell_refinement       'DENZO (Otwinowski, 1988)'
_computing_data_collection
;
MSC RAXIS11 Control Software (Molecular Structure Corporation, 1992)
;
_computing_data_reduction        DENZO
_computing_molecular_graphics    SHELXTL
_computing_publication_material  'SHELXTL (Bruker, 2001)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution
;
SHELXS86 (Sheldrick, 1985) and TEXSAN (Molecular Structure
Corporation, 1995)
;
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.949
_diffrn_measured_fraction_theta_max 0.949
_diffrn_measurement_device       'Rigaku R-AXIS'
_diffrn_measurement_method       '40 x 5\% \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  0.042
_diffrn_reflns_av_sigmaI/netI    0.0347
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            10171
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.04
_diffrn_standards_decay_%        0.00
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.290
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.183
_refine_diff_density_min         -0.179
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     171
_refine_ls_number_reflns         2173
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0517
_refine_ls_R_factor_gt           0.0421
_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^)+(0.0780P)^2^+0.2408P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1204
_refine_ls_wR_factor_ref         0.1264
_reflns_number_gt                1840
_reflns_number_total             2173
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            kj2003.cif
_cod_data_source_block           5
_cod_original_cell_volume        1300(3)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2209232