A Versatile and Practical Solvating Agent for Enantioselective Recognition and NMR Analysis of Protected Amines
Daniel P. Iwaniuk; Christian Wolf; Journal of Organic Chemistry 75 (2010) 6724–6727; doi:10.1021/jo101426a

data_4025716
_publ_contact_author_address
; 
Department of Chemistry
Georgetown University
37th and O Streets NW
Washington DC 20057
USA
;
_publ_contact_author_email       cw27@georgetown.edu
_publ_contact_author_fax         '(202) 687 6209'
_publ_contact_author_name        'Christian Wolf'
_publ_contact_author_phone       '(202) 687 3468'
_publ_section_title
;
 A Versatile and Practical Solvating Agent for Enantioselective
 Recognition and NMR Analysis of Protected Amines
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6724
_journal_page_last               6727
_journal_paper_doi               10.1021/jo101426a
_journal_volume                  75
_journal_year                    2010
_chemical_absolute_configuration syn
_chemical_formula_sum            'C36 H36 N4 O6'
_chemical_formula_weight         620.69
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 93.087(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.592(3)
_cell_length_b                   17.603(5)
_cell_length_c                   19.168(5)
_cell_measurement_reflns_used    13156
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      51.323
_cell_measurement_theta_min      4.628
_cell_volume                     3231.8(16)
_computing_cell_refinement       'SAINT, Bruker-AXS'
_computing_data_collection       'APEX, Bruker-AXS'
_computing_data_reduction        'SAINT, Bruker-AXS'
_computing_molecular_graphics    X-SEED,L.Barbour(1999):http://x-seed.net/
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Siemens SMART,Bruker APEXII CCD'
_diffrn_measurement_method       '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  0.0479
_diffrn_reflns_av_sigmaI/netI    0.0755
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            25303
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         1.57
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.9974
_exptl_absorpt_correction_T_min  0.4853
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS.G.Sheldrick(1999)
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.276
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1312
_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.46
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.521
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   1.6(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.977
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     855
_refine_ls_number_reflns         13156
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.977
_refine_ls_R_factor_all          0.0785
_refine_ls_R_factor_gt           0.0482
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0565P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1068
_refine_ls_wR_factor_ref         0.1170
_reflns_number_gt                9726
_reflns_number_total             13156
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo101426a_si_001.cif
_cod_data_source_block           g:\frames\guest\10132\work\p21
_cod_original_cell_volume        3231.6(15)
_cod_database_code               4025716