Novel Chiral Calix[4]arenes by Direct Asymmetric Epoxidation Reaction
Carlo Bonini; Lucia Chiummiento; Maria Funicello; Maria Teresa Lopardo; Paolo Lupattelli; Alessandro Laurita; Andrea Cornia; Journal of Organic Chemistry 73 (2008) 4233–4236; doi:10.1021/jo800301m

data_4023441
_publ_contact_author_address
;Department of Chemistry
Universita degli Studi della Basilicata
Via N. Sauro n. 85
85100 Potenza
Italy
;
_publ_contact_author_email       carlo.bonini@unibas.it
_publ_contact_author_fax         '+39 0971 202223'
_publ_contact_author_name        'Prof. Carlo Cesare Bonini'
_publ_contact_author_phone       '+39 0971 202209'
_publ_section_title
;
 Novel Chiral Calix[4]arenes by Direct Asymmetric Epoxidation Reaction
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4233
_journal_page_last               4236
_journal_paper_doi               10.1021/jo800301m
_journal_volume                  73
_journal_year                    2008
_chemical_absolute_configuration ad
_chemical_compound_source        synthesis
_chemical_formula_iupac          'C56 H60 O6'
_chemical_formula_moiety         'C56 H60 O6'
_chemical_formula_sum            'C56 H60 O6'
_chemical_formula_weight         829.04
_chemical_melting_point          423
_chemical_name_common            'trans,trans 1,3-bis-styrylepoxycalix[4]arene'
_chemical_name_systematic
5,17-bis-[(2R,3R)-3-phenyl-2-oxiranyl)-25,26,27,28-tetrapropyloxycalix[4]arene
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      5
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 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                 95.8354(12)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   25.7719(3)
_cell_length_b                   9.74588(16)
_cell_length_c                   18.1938(2)
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      72.1514
_cell_measurement_theta_min      4.0157
_cell_volume                     4546.05(10)
_computing_cell_refinement
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.31.2 (release 07-07-2006 CrysAlis171 .NET)
(compiled Jul 10 2006,00:11:42)
;
_computing_data_collection
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.31.2 (release 07-07-2006 CrysAlis171 .NET)
(compiled Jul 10 2006,00:11:42)
;
_computing_data_reduction
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.31.2 (release 07-07-2006 CrysAlis171 .NET)
(compiled Jul 10 2006,00:11:42)
;
_computing_molecular_graphics    'ORTEP3 (Farrugia, 1997)'
_computing_publication_material  'WINGX v1.70.01 (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Altomare, 1993)'
_diffrn_ambient_pressure         101
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.1241
_diffrn_measured_fraction_theta_full 0.943
_diffrn_measured_fraction_theta_max 0.943
_diffrn_measurement_details
;
  1 omega  -30.00   20.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -       -9.8862  -75.0000  120.0000    0.0000    0.0000 50

  2 omega  -33.00   13.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -       -9.8862  -45.0000    0.0000    0.0000    0.0000 46

  3 omega  -79.00  -33.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -       -9.8862  -45.0000    0.0000    0.0000    0.0000 46

  4 omega   36.00   82.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -       12.9962   45.0000  120.0000    0.0000    0.0000 46

  5 omega  -10.00   36.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -       12.9962  -45.0000  120.0000    0.0000    0.0000 46

  6 omega -158.00 -112.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -      -89.0000  -48.0000  220.0000    0.0000    0.0000 46

  7 omega -113.00  -66.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -      -89.0000  -38.0000  254.0000    0.0000    0.0000 47

  8 omega -162.00 -105.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -      -89.0000 -163.0000  319.0000    0.0000    0.0000 57

  9 omega -109.00  -59.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -      -89.0000  -75.0000  240.0000    0.0000    0.0000 50

 10 omega -158.00 -112.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -      -89.0000  -45.0000  120.0000    0.0000    0.0000 46

 11 omega  -68.00  -18.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -      -89.0000   75.0000    0.0000    0.0000    0.0000 50

 12 omega  -66.00  -20.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -      -89.0000   45.0000    0.0000    0.0000    0.0000 46

 13 omega -158.00 -112.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -      -89.0000  -45.0000  240.0000    0.0000    0.0000 46

 14 omega   31.00   77.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -      100.0000  -45.0000  120.0000    0.0000    0.0000 46

 15 omega   77.00  125.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -      100.0000 -132.0000   52.0000    0.0000    0.0000 48

 16 omega   77.00  123.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -      100.0000  -45.0000  240.0000    0.0000    0.0000 46

 17 omega   73.00  119.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -      100.0000 -120.0000  223.0000    0.0000    0.0000 46

 18 omega  123.00  169.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -      100.0000   45.0000    0.0000    0.0000    0.0000 46

 19 omega   29.00   79.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -      100.0000  -75.0000  120.0000    0.0000    0.0000 50
;
_diffrn_measurement_device_type  'XcaliburPX Ultra'
_diffrn_measurement_method       'omega scans'
_diffrn_orient_matrix_UB_11      0.0568751332
_diffrn_orient_matrix_UB_12      0.0073615316
_diffrn_orient_matrix_UB_13      -0.0191776128
_diffrn_orient_matrix_UB_21      0.0031337975
_diffrn_orient_matrix_UB_22      -0.1580903007
_diffrn_orient_matrix_UB_23      0.0006598721
_diffrn_orient_matrix_UB_31      -0.0193894806
_diffrn_orient_matrix_UB_32      -0.0030228385
_diffrn_orient_matrix_UB_33      -0.0829194542
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0163
_diffrn_reflns_av_sigmaI/netI    0.0236
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            13792
_diffrn_reflns_theta_full        72.30
_diffrn_reflns_theta_max         72.30
_diffrn_reflns_theta_min         4.02
_diffrn_source                   'Enhance (Cu) X-ray Source'
_diffrn_source_type              'XcaliburPX Ultra'
_diffrn_standards_decay_%        'not measured'
_diffrn_standards_interval_count 'not measured'
_diffrn_standards_interval_time  'not measured'
_diffrn_standards_number         'not measured'
_exptl_absorpt_coefficient_mu    0.607
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.211
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    .
_exptl_crystal_description       needle
_exptl_crystal_F_000             1776
_exptl_crystal_recrystallization_method n-esano
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.169
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.04(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     570
_refine_ls_number_reflns         7299
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.094
_refine_ls_R_factor_all          0.0422
_refine_ls_R_factor_gt           0.0340
_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^)+(0.0673P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0939
_refine_ls_wR_factor_ref         0.1022
_reflns_number_gt                6219
_reflns_number_total             7299
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo800301m-File001.cif
_cod_data_source_block           cornian3
_cod_original_sg_symbol_H-M      'C 2'
_cod_database_code               4023441