Optical Resolution of (\±)-1,2-Bis(2-methylphenyl)ethylene-1,2-diamine as a Chiral Framework for 2-Iminoimidazolidine with 2-Methylphenyl Pendant and the Guanidine-Catalyzed Asymmetric Michael Reaction of tert-Butyl Diphenyliminoacetate and Ethyl Acrylate
Akemi Ryoda; Nana Yajima; Toyokazu Haga; Takuya Kumamoto; Waka Nakanishi; Masatoshi Kawahata; Kentaro Yamaguchi; Tsutomu Ishikawa; Journal of Organic Chemistry 73 (2008) 133–141; doi:10.1021/jo701923z

data_4023171
_publ_contact_author_address
;Graduate School of Pharmaceutical Sciences
Chiba University
1-33 Yayoi-cho
Inage-ku
Chiba-shi
Chiba 263-8522
Japan
;
_publ_contact_author_email       benti@p.chiba-u.ac.jp
_publ_contact_author_fax         81(43)2902910
_publ_contact_author_name        'Professor Tsutomu Ishikawa'
_publ_contact_author_phone       81(43)2902910
_publ_section_title
;
 Optical Resolution of (\+-)-1,2-Bis(2-methylphenyl)ethylene-1,2-diamine
 as a Chiral Framework for 2-Iminoimidazolidine with 2-Methylphenyl
 Pendant and the Guanidine-Catalyzed Asymmetric Michael Reaction
 of tert-Butyl Diphenyliminoacetate and Ethyl Acrylate
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              133
_journal_page_last               141
_journal_paper_doi               10.1021/jo701923z
_journal_volume                  73
_journal_year                    2008
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C28 H33 N3 O'
_chemical_formula_sum            'C28 H33 N3 O'
_chemical_formula_weight         427.57
_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                   8.1113(12)
_cell_length_b                   14.058(2)
_cell_length_c                   21.632(3)
_cell_measurement_reflns_used    2530
_cell_measurement_temperature    173
_cell_measurement_theta_max      20.85
_cell_measurement_theta_min      2.38
_cell_volume                     2466.7(7)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Bruker, 1988)'
_computing_data_reduction        'SAINT (Bruker, 1998)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_method       '\f and \w 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  0.0361
_diffrn_reflns_av_sigmaI/netI    0.0449
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            11262
_diffrn_reflns_theta_full        24.70
_diffrn_reflns_theta_max         24.70
_diffrn_reflns_theta_min         1.73
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.070
_exptl_absorpt_correction_T_max  0.9895
_exptl_absorpt_correction_T_min  0.9724
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS Sheldrick 1996'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.151
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       cubic
_exptl_crystal_F_000             920
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.371
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   1(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     297
_refine_ls_number_reflns         4205
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0714
_refine_ls_R_factor_gt           0.0537
_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^)+(0.0873P)^2^+0.2324P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1368
_refine_ls_wR_factor_ref         0.1521
_reflns_number_gt                3254
_reflns_number_total             4205
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jo701923z-File002.cif
_cod_data_source_block           szwn014p212121
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
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               4023171