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_4027789
_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         'C22 H21 I O2'
_chemical_formula_sum            'C22 H21 I O2'
_chemical_formula_weight         444.29
_chemical_name_systematic
; 
 ? 
;
_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                 99.691(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.1646(6)
_cell_length_b                   8.3830(7)
_cell_length_c                   11.7462(7)
_cell_measurement_reflns_used    1563
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.3352
_cell_measurement_theta_min      2.8980
_cell_volume                     986.61(12)
_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 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0284
_diffrn_reflns_av_sigmaI/netI    0.0445
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            4459
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         2.90
_exptl_absorpt_coefficient_mu    1.634
_exptl_absorpt_correction_T_max  0.8156
_exptl_absorpt_correction_T_min  0.5986
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlis PRO (Agilent Technologies, 2011) 
;
_exptl_crystal_density_diffrn    1.496
_exptl_crystal_F_000             444
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.341
_refine_diff_density_min         -0.480
_refine_diff_density_rms         0.064
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.02(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     234
_refine_ls_number_reflns         2802
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0506
_refine_ls_R_factor_gt           0.0394
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0454P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0876
_refine_ls_wR_factor_ref         0.0950
_reflns_number_gt                2329
_reflns_number_total             2802
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo302223y_si_002.cif
_cod_data_source_block           111221_l_jb_31
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4027789