Synthesis of Indeno[1,2-c]furans via a Pd-Catalyzed Bicyclization of 2-Alkynyliodobenzene and Propargylic Alcohol
Jisong Jin; Yan Luo; Chao Zhou; Xiaopeng Chen; Qiaodong Wen; Ping Lu; Yanguang Wang; Journal of Organic Chemistry 77 (2012) 11368–11371; doi:10.1021/jo302223y

data_4027790
_publ_section_title
;
 Synthesis of Indeno[1,2-c]furans via a Pd-Catalyzed Bicyclization of
 2-Alkynyliodobenzene and Propargylic Alcohol
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              11368
_journal_page_last               11371
_journal_paper_doi               10.1021/jo302223y
_journal_volume                  77
_journal_year                    2012
_chemical_formula_moiety         'C31 H24 O'
_chemical_formula_sum            'C31 H24 O'
_chemical_formula_weight         412.50
_chemical_name_systematic
; 
 ? 
;
_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                71.274(6)
_cell_angle_beta                 74.494(6)
_cell_angle_gamma                88.393(5)
_cell_formula_units_Z            2
_cell_length_a                   9.5857(6)
_cell_length_b                   10.2270(6)
_cell_length_c                   12.6649(10)
_cell_measurement_reflns_used    2163
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.4967
_cell_measurement_theta_min      3.1763
_cell_volume                     1130.78(14)
_computing_cell_refinement       'CrysAlis PRO (Agilent Technologies, 2011)'
_computing_data_collection       'CrysAlis PRO'
_computing_data_reduction        'CrysAlis PRO'
_computing_molecular_graphics    'OLEX2 (Dolomanov et al., 2009)'
_computing_publication_material  OLEX2
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w 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  0.0254
_diffrn_reflns_av_sigmaI/netI    0.0384
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7091
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         3.18
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_T_max  0.9796
_exptl_absorpt_correction_T_min  0.9706
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlis PRO (Agilent Technologies, 2011) 
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.212
_exptl_crystal_description       block
_exptl_crystal_F_000             436
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.29
_refine_diff_density_max         0.162
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         4139
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0717
_refine_ls_R_factor_gt           0.0480
_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^)+(0.0682P)^2^+0.0654P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1180
_refine_ls_wR_factor_ref         0.1370
_reflns_number_gt                2940
_reflns_number_total             4139
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo302223y_si_003.cif
_cod_data_source_block           120330_l_jb_85
_cod_original_cell_volume        1130.79(13)
_cod_database_code               4027790