Highly stereoselective double (R)-phenylglycinol-induced cyclocondensation reactions of symmetric aryl bis(oxoacids).
Amat, Mercedes; Arróniz, Carlos; Molins, Elies; Escolano, Carmen; Bosch, Joan; Organic & biomolecular chemistry 9 (2011) 2175–2184; doi:10.1039/c0ob00970a

data_7151782
_publ_section_title
;
 Highly stereoselective double (R)-phenylglycinol-induced
 cyclocondensation reactions of symmetric aryl bis(oxoacids).
;
_journal_issue                   7
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2175
_journal_page_last               2184
_journal_paper_doi               10.1039/c0ob00970a
_journal_volume                  9
_journal_year                    2011
_chemical_absolute_configuration syn
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C31 H31 N3 O4'
_chemical_formula_sum            'C31 H32 N3 O4.5'
_chemical_formula_weight         518.59
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_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_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.2
_audit_creation_date             2007-03-12T17:43:29-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   9.102(2)
_cell_length_b                   18.341(5)
_cell_length_c                   32.012(8)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      22
_cell_measurement_theta_min      20
_cell_measurement_wavelength     0.71073
_cell_volume                     5344(2)
_computing_cell_refinement       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_collection       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      294(2)
_diffrn_detector                 'scintillation LiI'
_diffrn_detector_dtime           1.195
_diffrn_measured_fraction_theta_full 0.99
_diffrn_measured_fraction_theta_max 0.99
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Enraf Nonius CAD4'
_diffrn_measurement_method       'non-profiled omega/2theta scans'
_diffrn_orient_matrix_type
;
x-axis points to radiation source
the matrix is specified in reciprocal space
;
_diffrn_orient_matrix_UB_11      -0.023664
_diffrn_orient_matrix_UB_12      -0.025978
_diffrn_orient_matrix_UB_13      -0.026683
_diffrn_orient_matrix_UB_21      0.072646
_diffrn_orient_matrix_UB_22      -0.038856
_diffrn_orient_matrix_UB_23      0.007111
_diffrn_orient_matrix_UB_31      -0.078954
_diffrn_orient_matrix_UB_32      -0.028108
_diffrn_orient_matrix_UB_33      0.014608
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_unetI/netI     0.0985
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            5627
_diffrn_reflns_theta_full        25.72
_diffrn_reflns_theta_max         25.72
_diffrn_reflns_theta_min         2.22
_diffrn_source                   'Enraf Nonius FR590'
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.742
_exptl_absorpt_correction_T_min  0.302
_exptl_absorpt_correction_type   refdelf
_exptl_absorpt_process_details
;
(See: Walker, N. & Stuart, D. (1983) Acta Cryst. A39, 158-166)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             2200
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.536
_refine_diff_density_min         -0.648
_refine_diff_density_rms         0.138
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   2(4)
_refine_ls_extinction_coef       0.009(2)
_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   1.088
_refine_ls_hydrogen_treatment    calcd
_refine_ls_matrix_type           full
_refine_ls_number_parameters     701
_refine_ls_number_reflns         5627
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.087
_refine_ls_R_factor_all          0.2333
_refine_ls_R_factor_gt           0.1037
_refine_ls_shift/su_max          1.124
_refine_ls_shift/su_mean         0.026
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2595
_refine_ls_wR_factor_ref         0.3356
_reflns_number_gt                2603
_reflns_number_total             5627
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c0ob00970a.txt
_cod_data_source_block           jb61
_cod_database_code               7151782
_diffrn_standards_decay_corr_max 1
_diffrn_standards_decay_corr_min 1