An asymmetric ortholithiation approach to inherently chiral calix[4]arenes.
Herbert, Simon A.; Arnott, Gareth E.; Organic letters 11 (2009) 4986–4989; doi:10.1021/ol902238p

data_1504272
_publ_section_title
;
 An asymmetric ortholithiation approach to inherently chiral
 calix[4]arenes.
;
_journal_issue                   21
_journal_name_full               'Organic letters'
_journal_page_first              4986
_journal_page_last               4989
_journal_paper_doi               10.1021/ol902238p
_journal_volume                  11
_journal_year                    2009
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C70 H90 N O6 P, C2 H6 O, C Cl2 H2'
_chemical_formula_sum            'C73 H98 Cl2 N O7 P'
_chemical_formula_weight         1203.39
_chemical_name_common
'(<i>cR</i>)-11,17,23-tri-tert-butyl-5-((<i>S</i>)-4-isopropyl-4,5-dihydrooxazol-2-yl)-4-diphenylphosphoryl- 25,26,27,28-tetrapropoxycalix[4]arene'
_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                   13.6620(3)
_cell_length_b                   20.5772(4)
_cell_length_c                   24.4019(4)
_cell_measurement_reflns_used    7383
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.169
_cell_measurement_theta_min      2.238
_cell_volume                     6860.0(2)
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        SAINT
_computing_molecular_graphics
;
X-Seed (Barbour, 2001; Atwood and Barbour, 2003)
;
_computing_publication_material
;
X-Seed (Atwood and Barbour, 2003; Barbour, 2001)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker APEX CCD area-detector'
_diffrn_measurement_method       \w
_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  0.0502
_diffrn_reflns_av_sigmaI/netI    0.0624
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            38088
_diffrn_reflns_theta_full        28.00
_diffrn_reflns_theta_max         28.24
_diffrn_reflns_theta_min         1.71
_exptl_absorpt_coefficient_mu    0.170
_exptl_absorpt_correction_T_max  0.9750
_exptl_absorpt_correction_T_min  0.166
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.165
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2592
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.15
_refine_diff_density_max         1.209
_refine_diff_density_min         -0.710
_refine_diff_density_rms         0.059
_refine_ls_abs_structure_details 'Flack H D (1983); 6596 Friedel pairs'
_refine_ls_abs_structure_Flack   -0.05(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     799
_refine_ls_number_reflns         15731
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0760
_refine_ls_R_factor_gt           0.0548
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0690P)^2^+2.8815P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1293
_refine_ls_wR_factor_ref         0.1423
_reflns_number_gt                12539
_reflns_number_total             15737
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol902238p_si_002.cif
_cod_data_source_block           c:\frames
_cod_original_sg_symbol_H-M      P212121
_cod_database_code               1504272