Tetramerization of 3-Methyl-cyclopropene-3-carbonitrile: A Novel CN-Alder-ene Reaction
Roman V. Ashirov; Grigory A. Shamov; Olga A. Lodochnikova; I. A. Litvynov; Svetlana A. Appolonova; Vitaly V. Plemenkov; Journal of Organic Chemistry 73 (2008) 5985–5988; doi:10.1021/jo8005254

data_4023571
_publ_contact_author_address
; Institute of Organic &  Physical Chemistry  
Arbuzov Str.8 420088 Kazan  Russia
;
_publ_contact_author_email       olga@iopc.knc.ru
_publ_contact_author_fax         '+7 8432 732253'
_publ_contact_author_name        'Lodochnikova O.A.'
_publ_contact_author_phone       '+7 8432 727573'
_publ_section_title
;
 Tetramerization of 3-Methyl-cyclopropene-3-carbonitrile:
 A Novel CN-Alder-ene Reaction
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5985
_journal_page_last               5988
_journal_paper_doi               10.1021/jo8005254
_journal_volume                  73
_journal_year                    2008
_chemical_absolute_configuration unk
_chemical_formula_sum            'C20 H20 N4'
_chemical_formula_weight         316.40
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 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                   6.6748(5)
_cell_length_b                   16.397(4)
_cell_length_c                   16.741(6)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_volume                     1832.2(8)
_computing_cell_refinement       CAD4_(Enraf-Nonius,_1977)
_computing_data_collection       CAD4_(Enraf-Nonius,_1977)
_computing_data_reduction        process_MolEN_(Fair,_1990)
_computing_molecular_graphics    'PLATON (Spek, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    Direct_methods_(SIR,_Burla_et_al.,_1989)
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.976
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.1477
_diffrn_reflns_av_sigmaI/netI    0.1010
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3650
_diffrn_reflns_theta_full        74.33
_diffrn_reflns_theta_max         74.33
_diffrn_reflns_theta_min         3.77
_exptl_absorpt_coefficient_mu    0.546
_exptl_absorpt_correction_T_max  0.8986
_exptl_absorpt_correction_T_min  0.8532
_exptl_absorpt_correction_type   psi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.147
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plates
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.195
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.056
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.956
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         3437
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.956
_refine_ls_R_factor_all          0.1639
_refine_ls_R_factor_gt           0.0774
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1181P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1725
_refine_ls_wR_factor_ref         0.2137
_reflns_number_gt                1875
_reflns_number_total             3437
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo8005254-File001.cif
_cod_data_source_block           plem26
_cod_database_code               4023571