Synthesis of Bromoundecyl Resorc[4]arenes and Applications of the Cone Stereoisomer as Selector for Liquid Chromatography.
Corradi, Silvia; Mazzoccanti, Giulia; Ghirga, Francesca; Quaglio, Deborah; Nevola, Laura; Massera, Chiara; Ugozzoli, Franco; Giannini, Giuseppe; Ciogli, Alessia; D'Acquarica, Ilaria; The Journal of organic chemistry 83 (2018) 7683–7693; doi:10.1021/acs.joc.8b00488

data_4035604
_publ_section_title
;
 Synthesis of Bromoundecyl Resorc[4]arenes and Applications of the Cone
 Stereoisomer as Selector for Liquid Chromatography.
;
_journal_issue                   15
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              7683
_journal_page_last               7693
_journal_paper_doi               10.1021/acs.joc.8b00488
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C88 H132 Br4 O16'
_chemical_formula_sum            'C88 H132 Br4 O16'
_chemical_formula_weight         1765.57
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                99.057(6)
_cell_angle_beta                 99.848(6)
_cell_angle_gamma                98.921(6)
_cell_formula_units_Z            1
_cell_length_a                   12.197(3)
_cell_length_b                   18.407(5)
_cell_length_c                   10.556(3)
_cell_measurement_reflns_used    2034
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.174
_cell_measurement_theta_min      1.725
_cell_volume                     2265.2(11)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_publication_material
'SHELXL and WINGX (Farrugia, J. App. Cryst.2012, 45, 849-854'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SIR97 (Giacovazzo et al., 1999)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 8.192
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'BRUKER AXS SMART 1000'
_diffrn_measurement_method       omega-scan
_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  0.0947
_diffrn_reflns_av_unetI/netI     0.1941
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            21784
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        25.174
_diffrn_reflns_theta_max         25.174
_diffrn_reflns_theta_min         1.725
_exptl_absorpt_coefficient_mu    1.837
_exptl_absorpt_correction_T_max  1.000000
_exptl_absorpt_correction_T_min  0.749126
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS (Sheldrick, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.676
_refine_diff_density_min         -1.095
_refine_diff_density_rms         0.123
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     487
_refine_ls_number_reflns         8001
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.2636
_refine_ls_R_factor_gt           0.1116
_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^)+(0.1520P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2910
_refine_ls_wR_factor_ref         0.3495
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2431
_reflns_number_total             8001
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b00488_si_002.cif
_cod_data_source_block           shelx
_cod_database_code               4035604
_shelx_shelxl_version_number     2014/7
_shelx_res_checksum              62845
_shelx_hkl_checksum              58880