Multicomponent prins cyclization from allylsilyl alcohols leading to dioxaspirodecanes.
Barbero, Asunción; Diez-Varga, Alberto; Pulido, Francisco J.; Organic letters 15 (2013) 5234–5237; doi:10.1021/ol402425u

data_1556235
_publ_section_title
;
 Multicomponent prins cyclization from allylsilyl alcohols leading to
 dioxaspirodecanes.
;
_journal_issue                   20
_journal_name_full               'Organic letters'
_journal_page_first              5234
_journal_page_last               5237
_journal_paper_doi               10.1021/ol402425u
_journal_volume                  15
_journal_year                    2013
_chemical_formula_sum            'C22 H28 O4'
_chemical_formula_weight         356.44
_space_group_IT_number           62
_space_group_name_Hall           '-P 2ac 2n'
_space_group_name_H-M_alt        'P n m a'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P n m a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.5127(6)
_cell_length_b                   23.5267(13)
_cell_length_c                   9.6294(5)
_cell_measurement_reflns_used    5696
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      72.0757
_cell_measurement_theta_min      3.7545
_cell_volume                     1928.5(2)
_computing_cell_refinement
; 
'Sun May 12 22:51:17 2013' 
;
_computing_data_collection
; 
'Sun May 12 22:51:17 2013' 
;
_computing_data_reduction
; 
'Sun May 12 22:51:17 2013' 
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.4757
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0254
_diffrn_reflns_av_sigmaI/netI    0.0136
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            16221
_diffrn_reflns_theta_full        72.22
_diffrn_reflns_theta_max         72.22
_diffrn_reflns_theta_min         3.76
_exptl_absorpt_coefficient_mu    0.666
_exptl_absorpt_correction_T_max  0.885
_exptl_absorpt_correction_T_min  0.831
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.228
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.4037
_exptl_crystal_size_mid          0.3036
_exptl_crystal_size_min          0.2476
_refine_diff_density_max         0.272
_refine_diff_density_min         -0.476
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       0.0028(8)
_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   1.070
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     132
_refine_ls_number_reflns         1914
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0721
_refine_ls_R_factor_gt           0.0562
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1096P)^2^+0.4961P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1767
_refine_ls_wR_factor_ref         0.1965
_reflns_number_gt                1453
_reflns_number_total             1914
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol402425u_si_002.cif
_cod_data_source_block           Compound_2j_(aaanisa)
_cod_original_cell_volume        1928.53(19)
_cod_database_code               1556235