1,3-Dipolar cycloaddition reactions of azomethine ylides with a cellulose-derived chiral enone. A novel route for organocatalysts development.
Sarotti, Ariel M.; Spanevello, Rolando A.; Suárez, Alejandra G; Echeverría, Gustavo A; Piro, Oscar E.; Organic letters 14 (2012) 2556–2559; doi:10.1021/ol3008588

data_1507690
_publ_section_title
;
 1,3-Dipolar cycloaddition reactions of azomethine ylides with a
 cellulose-derived chiral enone. A novel route for organocatalysts
 development.
;
_journal_issue                   10
_journal_name_full               'Organic letters'
_journal_page_first              2556
_journal_page_last               2559
_journal_paper_doi               10.1021/ol3008588
_journal_volume                  14
_journal_year                    2012
_chemical_absolute_configuration ad
_chemical_formula_sum            'C17 H19 N O5'
_chemical_formula_weight         317.33
_chemical_name_systematic
; 
1S,2R,3S,5S,6S,8R-3-methyl-3-methoxycarbonyl-5-phenyl-9,
11-dioxa-4-azatricyclo[6.2.1.0^2,6^]undecan-7-one 
;
_space_group_IT_number           18
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2 2ab'
_symmetry_space_group_name_H-M   'P 21 21 2'
_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                   15.9699(4)
_cell_length_b                   13.9567(4)
_cell_length_c                   6.9126(2)
_cell_measurement_reflns_used    3330
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      73.8740
_cell_measurement_theta_min      4.2034
_cell_volume                     1540.73(7)
_computing_cell_refinement
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
;
_computing_data_collection
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
;
_computing_data_reduction
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
;
_computing_molecular_graphics    'ORTEP (Johnson, 1976)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      295(2)
_diffrn_detector_area_resol_mean 16.0604
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_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  0.0321
_diffrn_reflns_av_sigmaI/netI    0.0354
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            7063
_diffrn_reflns_theta_full        74.04
_diffrn_reflns_theta_max         74.04
_diffrn_reflns_theta_min         6.39
_diffrn_standards_decay_%        negligible
_exptl_absorpt_coefficient_mu    0.840
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72799
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.368
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.205
_refine_diff_density_min         -0.149
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.1(2)
_refine_ls_extinction_coef       0.0126(13)
_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   1.030
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     215
_refine_ls_number_reflns         2963
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0414
_refine_ls_R_factor_gt           0.0388
_refine_ls_shift/su_max          0.012
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0774P)^2^+0.0231P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1097
_refine_ls_wR_factor_ref         0.1143
_reflns_number_gt                2766
_reflns_number_total             2963
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            ol3008588_si_002.cif
_cod_data_source_block           s97
_cod_depositor_comments          'Adding full bibliography for 1507690.cif.'
_cod_original_sg_symbol_H-M      P21212
_cod_database_code               1507690