Synthesis of Organochalcogen Propargyl Aryl Ethers and Their Application in the Electrophilic Cyclization Reaction: An Efficient Preparation of 3-Halo-4-Chalcogen-2H-Benzopyrans
Benhur Godoi; Adriane Sperança; Davi F. Back; Ricardo Brandão; Cristina W. Nogueira; Gilson Zeni; Journal of Organic Chemistry 74 (2009) 3469–3477; doi:10.1021/jo900307k

data_4024510
_publ_section_title
;
Synthesis of Organochalcogen Propargyl Aryl Ethers and Their Application in
the Electrophilic Cyclization Reaction: An Efficient Preparation of
3-Halo-4-Chalcogen-2H-Benzopyrans
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3469
_journal_page_last               3477
_journal_paper_doi               10.1021/jo900307k
_journal_volume                  74
_journal_year                    2009
_chemical_formula_moiety         'C16 H13 I O Se'
_chemical_formula_sum            'C16 H13 I O Se'
_chemical_formula_weight         427.12
_chemical_melting_point          ?
_chemical_name_common            3-iodo-6-methyl-4-(phenylselenyl)-2H-chromene
_chemical_name_systematic
;
 3-iodo-6-methyl-4-(phenylselenyl)-2H-chromene
;
_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_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             2009-02-02T13:44:03-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                85.591(2)
_cell_angle_beta                 70.701(2)
_cell_angle_gamma                68.7780(10)
_cell_formula_units_Z            2
_cell_length_a                   8.4571(3)
_cell_length_b                   9.2494(3)
_cell_length_c                   10.8669(4)
_cell_measurement_reflns_used    5901
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.3575
_cell_measurement_theta_min      2.365
_cell_volume                     746.99(5)
_computing_cell_refinement       'BRUKER SAINT'
_computing_data_collection       'BRUKER APEX-II'
_computing_data_reduction        'BRUKER SOFTWARE'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 2000)'
_computing_publication_material  'SHELXL-97 (Shekdrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELX97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean none
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'X8 APEX II'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0241
_diffrn_reflns_av_unetI/netI     0.0237
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            12596
_diffrn_reflns_theta_full        26.44
_diffrn_reflns_theta_max         26.44
_diffrn_reflns_theta_min         1.99
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  .
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.569
_exptl_absorpt_correction_T_max  0.872
_exptl_absorpt_correction_T_min  0.6996
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
 XPREP (Bruker, 2006) was used to perform the Gaussian absorption
        correction based on the face-indexed crystal size.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.899
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.214
_exptl_crystal_size_mid          0.146
_exptl_crystal_size_min          0.136
_refine_diff_density_max         0.42
_refine_diff_density_min         -0.709
_refine_diff_density_rms         0.145
_refine_ls_extinction_coef       none
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.161
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         3084
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.161
_refine_ls_R_factor_all          0.0449
_refine_ls_R_factor_gt           0.0284
_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^)+(0.0529P)^2^+0.0481P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0804
_refine_ls_wR_factor_ref         0.1003
_reflns_number_gt                2383
_reflns_number_total             3084
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo900307k_si_001.cif
_cod_data_source_block           teste2
_cod_depositor_comments
;
The following automatic conversions were performed:

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

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4024510