Expedient Synthesis of C3-Symmetric Hexasubstituted Benzenes via Nicholas Reaction/[2 + 2 + 2] Cycloaddition. New Platforms for Molecular Recognition.
Carrillo, Romen; Martín, Tomás; López-Rodríguez, Matías; Pinacho Crisóstomo, Fernando; Organic letters 16 (2014) 552–555; doi:10.1021/ol403428p

data_1513400
_publ_section_title
;
 Expedient Synthesis of C3-Symmetric Hexasubstituted Benzenes via Nicholas
 Reaction/[2 + 2 + 2] Cycloaddition. New Platforms for Molecular
 Recognition.
;
_journal_issue                   2
_journal_name_full               'Organic letters'
_journal_page_first              552
_journal_page_last               555
_journal_paper_doi               10.1021/ol403428p
_journal_volume                  16
_journal_year                    2014
_chemical_formula_moiety         'C18 H24 O3'
_chemical_formula_sum            'C18 H24 O3'
_chemical_formula_weight         288.37
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                89.26(3)
_cell_angle_beta                 76.85(4)
_cell_angle_gamma                66.87(4)
_cell_formula_units_Z            2
_cell_length_a                   8.676(3)
_cell_length_b                   9.259(4)
_cell_length_c                   10.498(4)
_cell_measurement_temperature    293(2)
_cell_volume                     752.4(6)
_computing_cell_refinement       'CrysAlisPro (Oxford Diffraction Ltd., 2010)'
_computing_data_collection       'CrysAlisPro (Oxford Diffraction Ltd., 2010)'
_computing_data_reduction        'CrysAlisPro (Oxford Diffraction Ltd., 2010)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  ' WINGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR2004 (Burla et al., 2005)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.5953
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device_type  'Supernova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54180
_diffrn_reflns_av_R_equivalents  0.0414
_diffrn_reflns_av_sigmaI/netI    0.0230
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            11743
_diffrn_reflns_theta_full        73.62
_diffrn_reflns_theta_max         73.62
_diffrn_reflns_theta_min         5.71
_exptl_absorpt_coefficient_mu    0.677
_exptl_absorpt_correction_T_max  0.912
_exptl_absorpt_correction_T_min  0.882
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlis PRO, Oxford Diffraction, 2007'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.273
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'irregular shaped'
_exptl_crystal_F_000             312
_exptl_crystal_size_max          .22
_exptl_crystal_size_mid          .18
_exptl_crystal_size_min          .15
_refine_diff_density_max         0.216
_refine_diff_density_min         -0.175
_refine_diff_density_rms         0.034
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2957
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0424
_refine_ls_R_factor_gt           0.0404
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0634P)^2^+0.1333P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1144
_refine_ls_wR_factor_ref         0.1162
_reflns_number_gt                2797
_reflns_number_total             2957
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol403428p_si_002.cif
_cod_data_source_block           compound5
_cod_original_cell_volume        752.4(5)
_cod_database_code               1513400