Ytterbium(III) triflate catalyzed tandem Friedel-Crafts alkylation/hydroarylation of propargylic alcohols with phenols as an expedient route to indenols.
Zhang, Xiaoxiang; Teo, Wan Teng; Chan, Philip Wai Hong; Organic letters 11 (2009) 4990–4993; doi:10.1021/ol901981s

data_1504221
_publ_section_title
;
 Ytterbium(III) triflate catalyzed tandem Friedel-Crafts
 alkylation/hydroarylation of propargylic alcohols with phenols as an
 expedient route to indenols.
;
_journal_issue                   21
_journal_name_full               'Organic letters'
_journal_page_first              4990
_journal_page_last               4993
_journal_paper_doi               10.1021/ol901981s
_journal_volume                  11
_journal_year                    2009
_chemical_formula_moiety         'C29 H22 O2'
_chemical_formula_sum            'C29 H22 O2'
_chemical_formula_weight         402.47
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 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                 118.749(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   25.5017(11)
_cell_length_b                   10.0101(4)
_cell_length_c                   18.5411(9)
_cell_measurement_reflns_used    7022
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.48
_cell_measurement_theta_min      2.23
_cell_volume                     4149.6(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0478
_diffrn_reflns_av_sigmaI/netI    0.0472
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            32694
_diffrn_reflns_theta_full        31.18
_diffrn_reflns_theta_max         31.18
_diffrn_reflns_theta_min         1.82
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  0.9781
_exptl_absorpt_correction_T_min  0.9735
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1696
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.432
_refine_diff_density_min         -0.501
_refine_diff_density_rms         0.160
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         6667
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.088
_refine_ls_R_factor_all          0.0883
_refine_ls_R_factor_gt           0.0515
_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^)+(0.0902P)^2^+0.5238P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1372
_refine_ls_wR_factor_ref         0.1701
_reflns_number_gt                4578
_reflns_number_total             6667
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol901981s_si_002.cif
_cod_data_source_block           chan40
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               1504221