Regioselective Formation of Tetrahydroselenophenes via 5-exo-dig-Cyclization of 1-Butylseleno-4-alkynes
Gai, Rafaela M.; Schumacher, Ricardo F.; Back, Davi F.; Zeni, Gilson; Organic Letters 14 (2012) 6072–6075; doi:10.1021/ol302919b

data_1508779
_publ_section_title
;
 Regioselective Formation of Tetrahydroselenophenes via
 5-exo-dig-Cyclization of 1-Butylseleno-4-alkynes
;
_journal_coden_ASTM              ORLEF7
_journal_issue                   23
_journal_name_full               'Organic Letters'
_journal_page_first              6072
_journal_page_last               6075
_journal_paper_doi               10.1021/ol302919b
_journal_volume                  14
_journal_year                    2012
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C15 H13 I Se'
_chemical_formula_sum            'C15 H13 I Se'
_chemical_formula_weight         399.11
_chemical_melting_point          ?
_chemical_name_common            2-(iodo(naphthalen-2-yl)methylene)tetrahydros
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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             2012-09-21T19:42:57-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   8.6754(3)
_cell_length_b                   14.6380(5)
_cell_length_c                   21.7393(8)
_cell_measurement_reflns_used    9982
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.2225
_cell_measurement_theta_min      2.334
_cell_volume                     2760.68(17)
_computing_cell_refinement       'BRUKER SANT'
_computing_data_collection       'BRUKER APEX-II'
_computing_data_reduction        'BRUKER SOFTWARE'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 2000)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXL97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean none
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0371
_diffrn_reflns_av_unetI/netI     0.03
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            37130
_diffrn_reflns_theta_full        27.18
_diffrn_reflns_theta_max         27.18
_diffrn_reflns_theta_min         2.33
_diffrn_standards_decay_%        none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_number         none
_exptl_absorpt_coefficient_mu    4.932
_exptl_absorpt_correction_T_max  0.6212
_exptl_absorpt_correction_T_min  0.4184
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   XPREP
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.921
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1520
_exptl_crystal_size_max          0.688
_exptl_crystal_size_mid          0.665
_exptl_crystal_size_min          0.532
_refine_diff_density_max         0.98
_refine_diff_density_min         -0.727
_refine_diff_density_rms         0.082
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.025(13)
_refine_ls_extinction_coef       none
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     274
_refine_ls_number_reflns         6131
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.046
_refine_ls_R_factor_gt           0.0348
_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^)+(0.0369P)^2^+2.6830P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0809
_refine_ls_wR_factor_ref         0.0852
_reflns_number_gt                5089
_reflns_number_total             6131
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol302919b_si_002.cif
_cod_data_source_block           p212121
_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 1891 2012-01-12 08:04:46Z andrius 

The following automatic conversions were performed:

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

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 

 Updated bibliographic information.

 Antanas Vaitkus,
 2019-09-20
;
_cod_original_sg_symbol_Hall     'P2ac 2ab'
_cod_original_sg_symbol_H-M      P212121
_cod_database_code               1508779