Iron-Catalyzed Cyclization of Alkynols with Diorganyl Diselenides: Synthesis of 2,5-Dihydrofuran, 3,6-Dihydro-2H-pyran, and 2,5-Dihydro-1H-pyrrole Organoselanyl Derivatives.
Casola, Kamila K.; Back, Davi F.; Zeni, Gilson; The Journal of organic chemistry 80 (2015) 7702–7712; doi:10.1021/acs.joc.5b01448

data_4031300
_publ_section_title
;
 Iron-Catalyzed Cyclization of Alkynols with Diorganyl Diselenides:
 Synthesis of 2,5-Dihydrofuran, 3,6-Dihydro-2H-pyran, and
 2,5-Dihydro-1H-pyrrole Organoselanyl Derivatives.
;
_journal_issue                   15
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              7702
_journal_page_last               7712
_journal_paper_doi               10.1021/acs.joc.5b01448
_journal_volume                  80
_journal_year                    2015
_chemical_formula_moiety         'C29 H30 O Se2'
_chemical_formula_sum            'C29 H30 O Se2'
_chemical_formula_weight         552.45
_chemical_melting_point          ?
_chemical_name_common
2-phenyl-3,4-bis(p-tolylselanyl)-1-oxaspiro[4.5]dec-3-ene
_chemical_name_systematic
;
2-phenyl-3,4-bis(p-tolylselanyl)-1-oxaspiro[4.5]dec-3-ene
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_creation_date             2015-04-09T11:21:13-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 102.150(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.6511(4)
_cell_length_b                   30.2073(18)
_cell_length_c                   12.8484(8)
_cell_measurement_reflns_used    3178
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      20.666
_cell_measurement_theta_min      2.759
_cell_volume                     2523.6(3)
_computing_cell_refinement       'BRUKER SANT'
_computing_data_collection       'Bruker Instrument Service v2012.10.0.0'
_computing_data_reduction        'BRUKER SOFTWARE'
_computing_molecular_graphics    'Diamond (version 3.2i; Crystal Impact GbR, Bo'
_computing_publication_material  'APEX2 (version 2012.10-0; Bruker, 2012)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXL97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker X8 Kappa APEX II diffractometer'
_diffrn_measurement_method       '0.5 \% \w & \f scans'
_diffrn_radiation_monochromator  'graphite crystal'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0885
_diffrn_reflns_av_unetI/netI     0.0623
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       38
_diffrn_reflns_limit_k_min       -38
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            37385
_diffrn_reflns_theta_full        27.24
_diffrn_reflns_theta_max         27.24
_diffrn_reflns_theta_min         1.35
_diffrn_source                   'sealed ceramic X ray tube'
_diffrn_standards_decay_%        none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_number         none
_exptl_absorpt_coefficient_mu    2.949
_exptl_absorpt_correction_T_max  0.6410
_exptl_absorpt_correction_T_min  0.5651
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
SADABS (version 2012/1; Bruker, 2012) was used to perform the numerical
        absorption correction based on the indexed faces of the crystal.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.454
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1120
_exptl_crystal_size_max          0.553
_exptl_crystal_size_mid          0.173
_exptl_crystal_size_min          0.152
_refine_diff_density_max         0.818
_refine_diff_density_min         -1.002
_refine_diff_density_rms         0.12
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         5633
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0868
_refine_ls_R_factor_gt           0.0415
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0586P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0971
_refine_ls_wR_factor_ref         0.1255
_reflns_number_gt                3589
_reflns_number_total             5633
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo5b01448_si_002.cif
_cod_data_source_block           test1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value 'none' was changed to '?' - the value
is undefined or not given.

'_exptl_crystal_density_meas' value 'none' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3271 2015-04-21 07:52:19Z andrius 

 Adding full bibliography for 4031300.cif.
;
_cod_original_sg_symbol_Hall     -P2yn
_cod_original_sg_symbol_H-M      P21/n
_cod_database_code               4031300