Solvent-Free Thermal and Microwave-Assisted [3 + 2] Cycloadditions between Stabilized Azomethine Ylides and Nitrostyrenes. An Experimental and Theoretical Study
Ana Arrieta; Dorleta Otaegui; Aizpea Zubia; Fernando P. Cossío; Ángel Díaz-Ortiz; Antonio de la Hoz; M. Antonia Herrero; Pilar Prieto; Concepción Foces-Foces; José L. Pizarro; María I. Arriortúa; Journal of Organic Chemistry 72 (2007) 4313–4322; doi:10.1021/jo062672z

data_4022861
_publ_contact_author_address
;                                           
     Instituto Rocasolano, CSIC
     Departamento de Cristalograf\'ia
     Serrano 119
     E-28006 Madrid
     Spain
;
_publ_contact_author_email       cfoces@iqfr.csic.es
_publ_contact_author_fax         34-91-5641431
_publ_contact_author_name        'Foces-Foces, C.'
_publ_contact_author_phone       34-91-5619400
_publ_section_title
;
 Solvent-Free Thermal and Microwave-Assisted [3 + 2] Cycloadditions
 between Stabilized Azomethine Ylides and Nitrostyrenes.
 An Experimental and Theoretical Study
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4313
_journal_page_last               4322
_journal_paper_doi               10.1021/jo062672z
_journal_volume                  72
_journal_year                    2007
_chemical_formula_sum            'C22 H24 N2 O6'
_chemical_formula_weight         412.43
_chemical_name_systematic
;
 2R*,3R*,4S*,5S*)-2-methoxycarbonyl-3-(4-methoxyphenyl)-5-
(4-methylphenyl)-4-nitropyrrolidine
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_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                90.737(5)
_cell_angle_beta                 98.140(6)
_cell_angle_gamma                97.005(5)
_cell_formula_units_Z            4
_cell_length_a                   9.7474(12)
_cell_length_b                   14.4829(14)
_cell_length_c                   15.887(2)
_cell_measurement_reflns_used    9230
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      2.60
_cell_volume                     2202.6(4)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius BV, 2000)'
_computing_data_reduction
'HKL Denzo and Scalepak (Otwinowski & Minor, 1997)'
_computing_molecular_graphics
'WinGX (Farrugia, 1999), PLATON (Spek, 2003) and MERCURY (Bruno et al., 2002)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device       '95mm CCD camera on \k-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_radiation_monochromator  'horizontally mounted graphite crystal'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0443
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            9980
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         2.60
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.244
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             872
_refine_diff_density_max         0.323
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       0.041(4)
_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   1.088
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     542
_refine_ls_number_reflns         9980
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.088
_refine_ls_R_factor_all          0.1019
_refine_ls_R_factor_gt           0.0816
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0866P)^2^+1.7100P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2069
_refine_ls_wR_factor_ref         0.2208
_reflns_number_gt                8036
_reflns_number_total             9980
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo062672zsi20070112_010850.cif
_cod_data_source_block           epimer(8)
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_database_code               4022861