Iron-Catalyzed Tandem Conia-Ene/Friedel-Crafts Reactions of o-Alkynyldihydrochalcones: Access to Benzo[b]fluorenes.
Akbar, Sikkandarkani; Srinivasan, Kannupal; The Journal of organic chemistry 81 (2016) 1229–1236; doi:10.1021/acs.joc.5b02391

data_4031912
_publ_section_title
;
 Iron-Catalyzed Tandem Conia-Ene/Friedel-Crafts Reactions of
 o-Alkynyldihydrochalcones: Access to Benzo[b]fluorenes.
;
_journal_issue                   3
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              1229
_journal_page_last               1236
_journal_paper_doi               10.1021/acs.joc.5b02391
_journal_volume                  81
_journal_year                    2016
_chemical_formula_moiety         'C27 H28 O6'
_chemical_formula_sum            'C27 H28 O6'
_chemical_formula_weight         448.49
_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                98.4540(10)
_cell_angle_beta                 105.8140(10)
_cell_angle_gamma                91.2700(10)
_cell_formula_units_Z            2
_cell_length_a                   8.9759(2)
_cell_length_b                   9.7135(2)
_cell_length_c                   14.1700(3)
_cell_measurement_reflns_used    4856
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.49
_cell_measurement_theta_min      1.51
_cell_volume                     1173.25(4)
_computing_cell_refinement       APEX2
_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_molecular_graphics    'ORTEP3 (Farrugia, 2012)'
_computing_publication_material  'SHELXL97 and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type
'Bruker SMART APEXII area-detector diffractometer'
_diffrn_measurement_method       '\w and \f 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  0.0268
_diffrn_reflns_av_sigmaI/netI    0.0246
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            17039
_diffrn_reflns_theta_full        26.49
_diffrn_reflns_theta_max         26.49
_diffrn_reflns_theta_min         1.51
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.9824
_exptl_absorpt_correction_T_min  0.9737
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(<i>SADABS</i>; Bruker, 2008)'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.270
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Blcok
_exptl_crystal_F_000             476
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.220
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.033
_refine_ls_extinction_coef       0.0105(19)
_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   0.980
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     304
_refine_ls_number_reflns         4856
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.980
_refine_ls_R_factor_all          0.0725
_refine_ls_R_factor_gt           0.0453
_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^)+(0.0584P)^2^+0.3206P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1138
_refine_ls_wR_factor_ref         0.1327
_reflns_number_gt                3278
_reflns_number_total             4856
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo5b02391_si_002.cif
_cod_data_source_block           fin
_cod_depositor_comments
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The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' according to
/usr/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas 
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_cod_database_code               4031912