Aza-Crown Macrocycles as Chiral Solvating Agents for Mandelic Acid Derivatives
Thomas P. Quinn; Philip D. Atwood; Joseph M. Tanski; Tyler F. Moore; J. Frantz Folmer-Andersen; Journal of Organic Chemistry 76 (2011) 10020–10030; doi:10.1021/jo2018203

data_4026791
_publ_contact_author             'Frantz Folmer-Andersen'
_publ_contact_author_email       andersef@newpaltz.edu
_publ_section_title
;
 Aza-Crown Macrocycles as Chiral Solvating Agents for Mandelic Acid
 Derivatives
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              10020
_journal_page_last               10030
_journal_paper_doi               10.1021/jo2018203
_journal_volume                  76
_journal_year                    2011
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C28 H40 N2 O5'
_chemical_formula_sum            'C28 H40 N2 O5'
_chemical_formula_weight         484.62
_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                   8.3568(3)
_cell_length_b                   14.9131(5)
_cell_length_c                   20.9098(7)
_cell_measurement_reflns_used    8320
_cell_measurement_temperature    125(2)
_cell_measurement_theta_max      67.34
_cell_measurement_theta_min      3.64
_cell_volume                     2605.90(15)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      125(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_radiation_source         'Cu IuS micro-focus source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0505
_diffrn_reflns_av_sigmaI/netI    0.0397
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            20643
_diffrn_reflns_theta_full        67.98
_diffrn_reflns_theta_max         67.98
_diffrn_reflns_theta_min         3.64
_exptl_absorpt_coefficient_mu    0.677
_exptl_absorpt_correction_T_max  0.9669
_exptl_absorpt_correction_T_min  0.8384
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.235
_exptl_crystal_description       block
_exptl_crystal_F_000             1048
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.152
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details
'Flack H D (1983), Acta Cryst. A39, 876-881, 2001 Friedel pairs'
_refine_ls_abs_structure_Flack   0.09(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     322
_refine_ls_number_reflns         4669
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0422
_refine_ls_R_factor_gt           0.0370
_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^)+(0.0583P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0906
_refine_ls_wR_factor_ref         0.0939
_reflns_number_gt                4247
_reflns_number_total             4669
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo2018203_si_004.cif
_cod_data_source_block           cu_fa1123c
_cod_original_sg_symbol_Hall     P2ac2ab
_cod_database_code               4026791