Endo-benzonorbornen-2-ol as an efficient non-natural chiral auxiliary in the asymmetric aza-Diels–Alder reactions between cyclopentadiene and (1-phenylethyl)iminoacetates
Sousa, Carlos Alberto; Maestro, Miguel Ángel; Garcia-Mera, Xerardo; Rodriguez-Borges, José Enrique; RSC Adv.  (2014) –; doi:10.1039/C4RA11143E

data_7218515
_publ_section_title
;
 Endo-benzonorbornen-2-ol as an efficient non-natural chiral auxiliary in
 the asymmetric aza-Diels--Alder reactions between cyclopentadiene and
 (1-phenylethyl)iminoacetates
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C4RA11143E
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C26 H27 N O2'
_chemical_formula_sum            'C26 H27 N O2'
_chemical_formula_weight         385.49
_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                   5.8560(4)
_cell_length_b                   15.3344(11)
_cell_length_c                   22.6230(16)
_cell_measurement_temperature    102(2)
_cell_volume                     2031.5(2)
_computing_cell_refinement       'SAINT V7.68A (Bruker, 2009) in Apex2 suite'
_computing_data_collection       'Apex2, Bruker Instr. Service v2010, 1-2'
_computing_data_reduction        'SAINT and XPREP Version 2008/2 (Bruker)'
_computing_structure_refinement  'XL Version 2008/4'
_computing_structure_solution    'XS Version 2008/1'
_diffrn_ambient_temperature      102(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0891
_diffrn_reflns_av_sigmaI/netI    0.0558
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            79365
_diffrn_reflns_theta_full        26.40
_diffrn_reflns_theta_max         26.40
_diffrn_reflns_theta_min         1.60
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  0.9976
_exptl_absorpt_correction_T_min  0.9616
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 Siemens SADABS program multi-scan Version 2008/1
 Blessing, Acta Cryst. (1995) A51 33-38 
;
_exptl_crystal_colour            colourles
_exptl_crystal_density_diffrn    1.260
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.232
_refine_diff_density_min         -0.233
_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   -0.3(14)
_refine_ls_extinction_coef       0.0157(17)
_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   1.063
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     279
_refine_ls_number_reflns         4065
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0732
_refine_ls_R_factor_gt           0.0402
_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^)+(0.0618P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0894
_refine_ls_wR_factor_ref         0.1082
_reflns_number_gt                2972
_reflns_number_total             4065
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ra11143e2.cif
_cod_data_source_block           anc1
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               7218515