Room-temperature metal-free electrophilic 5-endo-selective iodocarbocyclization of 1,5-enynes.
Pradal, Alexandre; Nasr, Alexandre; Toullec, Patrick Y.; Michelet, Veronique; Organic letters 12 (2010) 5222–5225; doi:10.1021/ol102257z

data_1503291
_publ_section_title
;
 Room-temperature metal-free electrophilic 5-endo-selective
 iodocarbocyclization of 1,5-enynes.
;
_journal_issue                   22
_journal_name_full               'Organic letters'
_journal_page_first              5222
_journal_page_last               5225
_journal_paper_doi               10.1021/ol102257z
_journal_volume                  12
_journal_year                    2010
_chemical_formula_moiety         'C25 H37 I O Si'
_chemical_formula_sum            'C25 H37 I O Si'
_chemical_formula_weight         508.54
_space_group_IT_number           7
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      7
_symmetry_space_group_name_Hall  'P -2yc'
_symmetry_space_group_name_H-M   'P 1 c 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                 109.045(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   11.0609(8)
_cell_length_b                   8.0727(7)
_cell_length_c                   14.9313(15)
_cell_measurement_reflns_used    117
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      21.8
_cell_measurement_theta_min      5.5
_cell_volume                     1260.26(19)
_computing_cell_refinement       'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction        'EvalCCD (Duisenberg & Schreurs 1990-2000)'
_computing_molecular_graphics    'DIAMOND. Crystal Impact GbR, Bonn, Germany'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Giacovazzo et al, 1993)'
_diffrn_ambient_temperature      200(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_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  0.0400
_diffrn_reflns_av_sigmaI/netI    0.0386
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            30608
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         30.00
_diffrn_reflns_theta_min         3.23
_exptl_absorpt_coefficient_mu    1.330
_exptl_absorpt_correction_T_max  0.864
_exptl_absorpt_correction_T_min  0.695
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
SADABS, Bruker AXS Inc., Madison, 
Wisconsin, USA. 
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.340
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       stick
_exptl_crystal_F_000             524
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.570
_refine_diff_density_min         -0.617
_refine_diff_density_rms         0.059
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.056(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     310
_refine_ls_number_reflns         6749
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0487
_refine_ls_R_factor_gt           0.0293
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0311P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0578
_refine_ls_wR_factor_ref         0.0631
_reflns_number_gt                5297
_reflns_number_total             6749
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            ol102257z_si_001.cif
_cod_data_source_block           ans53
_cod_original_sg_symbol_H-M      'P c'
_cod_database_code               1503291