Palladium-Catalyzed Annulation of 2-(1-Alkynyl)biphenyls with Aryl Iodides to Disubstituted Methylidenefluorenes.
Chin-Chau Chen; Shyh-Chyun Yang; Ming-Jung Wu; Journal of Organic Chemistry 76 (2011) 7631–7631; doi:10.1021/jo9017556

data_4026592
_publ_section_title
;
 Palladium-Catalyzed Annulation of 2-(1-Alkynyl)biphenyls with Aryl
 Iodides to Disubstituted Methylidenefluorenes.
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7631
_journal_page_last               7631
_journal_paper_doi               10.1021/jo9017556
_journal_volume                  76
_journal_year                    2011
_chemical_formula_moiety         'C24 H22 O1'
_chemical_formula_sum            'C24 H22 O'
_chemical_formula_weight         326.42
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 102.113(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.0199(4)
_cell_length_b                   7.6276(3)
_cell_length_c                   12.0388(5)
_cell_measurement_reflns_used    6307
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      25.35
_cell_measurement_theta_min      2.037
_cell_volume                     899.61(6)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction        'HKL Denzo and Scalepack'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_diffrn_ambient_temperature      200(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_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  0.0418
_diffrn_reflns_av_sigmaI/netI    0.0531
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4848
_diffrn_reflns_theta_full        25.38
_diffrn_reflns_theta_max         25.38
_diffrn_reflns_theta_min         2.08
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_T_max  1.0264
_exptl_absorpt_correction_T_min  0.9014
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 ?
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.205
_exptl_crystal_description       prism
_exptl_crystal_F_000             348
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.293
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.089
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   4(3)
_refine_ls_extinction_coef       0.32(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.147
_refine_ls_hydrogen_treatment    fixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         2726
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.146
_refine_ls_R_factor_all          0.0612
_refine_ls_R_factor_gt           0.0497
_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^)+(0.0806P)^2^+0.0335P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1222
_refine_ls_wR_factor_ref         0.1394
_reflns_number_gt                2419
_reflns_number_total             2726
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo9017556_si_001.cif
_cod_data_source_block           8518
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4026592