Synthesis of Mono-O-alkylated Homooxacalix[3]arene and a Protection-Deprotection Strategy for Homooxacalix[3]arene.
Wu, Chong; Ikejiri, Yusuke; Zeng, Xi; Elsegood, Mark R. J.; Redshaw, Carl; Yamato, Takehiko; Organic letters  (2016) –; doi:10.1021/acs.orglett.6b03338

data_1544961
_publ_section_title
;
 Synthesis of Mono-O-alkylated Homooxacalix[3]arene and a
 Protection-Deprotection Strategy for Homooxacalix[3]arene.
;
_journal_name_full               'Organic letters'
_journal_paper_doi               10.1021/acs.orglett.6b03338
_journal_year                    2016
_chemical_formula_moiety         'C39 H54 O6'
_chemical_formula_sum            'C39 H54 O6'
_chemical_formula_weight         618.82
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                90
_cell_angle_beta                 100.3861(13)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   22.6735(16)
_cell_length_b                   14.6312(10)
_cell_length_c                   10.9828(8)
_cell_measurement_reflns_used    4502
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      26.81
_cell_measurement_theta_min      2.30
_cell_volume                     3583.7(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL and local programs'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXS-97 (sheldrick, 1997)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker SMART 1000 CCD diffractometer'
_diffrn_measurement_method       '\w rotation with narrow frames'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0551
_diffrn_reflns_av_unetI/netI     0.0639
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            23451
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_min         1.665
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  0.997
_exptl_absorpt_correction_T_min  0.960
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, v. 2.08, Sheldrick, G.M., (2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.147
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       lath
_exptl_crystal_F_000             1344
_exptl_crystal_size_max          0.550
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.672
_refine_diff_density_min         -0.329
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     422
_refine_ls_number_reflns         7031
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.006
_refine_ls_R_factor_all          0.1212
_refine_ls_R_factor_gt           0.0573
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0737P)^2^+2.7932P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1404
_refine_ls_wR_factor_ref         0.1808
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3880
_reflns_number_total             7031
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b03338_si_002.cif
_cod_data_source_block           cr129
_cod_database_code               1544961
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_min   0.960
_shelx_estimated_absorpt_t_max   0.997
_shelx_res_checksum              80987
_shelx_hkl_checksum              57532