Syn- and Anti-Selective Prins Cyclizations of δ,ε-Unsaturated Ketones to 1,3-Halohydrins with Lewis Acids
R. Brandon Miles; Chad E. Davis; Robert M. Coates; Journal of Organic Chemistry 71 (2006) 1493–1501; doi:10.1021/jo052142n

data_4021497
_publ_contact_author_address
;Department of Chemistry
University of Illinois 
600 South Mathews Avenue 
Urbana, Illinois  61801 
USA 
;
_publ_contact_author_email       coates@scs.uiuc.edu
_publ_contact_author_fax         '1  217 244 8024'
_publ_contact_author_name        ' Robert M. Coates'
_publ_section_title
;
 Syn- and Anti-Selective Prins Cyclizations of \d,\e-Unsaturated
 Ketones to 1,3-Halohydrins with Lewis Acids
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1493
_journal_page_last               1501
_journal_paper_doi               10.1021/jo052142n
_journal_volume                  71
_journal_year                    2006
_chemical_absolute_configuration ad
_chemical_compound_source        synthesis
_chemical_formula_moiety         'C14 H25 Cl O'
_chemical_formula_sum            'C14 H25 Cl O'
_chemical_formula_weight         244.79
_chemical_melting_point          317
_chemical_name_common
(1S,2R,3R,6S,9R)-3-Chloro-2,5,5,9-tetramethylbicyclo[4.4.0]decan-1-ol
_chemical_name_systematic
(1S,2R,3R,6S,9R)-3-Chloro-2,5,5,9-tetramethylbicyclo[4.4.0]decan-1-ol
_space_group_IT_number           169
_space_group_name_Hall           'P 61'
_space_group_name_H-M_alt        'P 61'
_symmetry_cell_setting           trigonal
_symmetry_Int_Tables_number      169
_symmetry_space_group_name_Hall  'P 61'
_symmetry_space_group_name_H-M   'P 61'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
; 
2003-08-21   text and data added, srw 
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_formula_units_Z            18
_cell_length_a                   12.447(6)
_cell_length_b                   12.447(6)
_cell_length_c                   49.29(5)
_cell_measurement_reflns_used    937
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      19.8
_cell_measurement_theta_min      1.9
_cell_volume                     6613(8)
_computing_cell_refinement       'SAINT V6.22 (Bruker, 2001)'
_computing_data_collection       'SMART V5.625 (Bruker, 2001)'
_computing_data_reduction        'SAINT V6.22 (Bruker, 2001)'
_computing_molecular_graphics    'SHELXTL V6.10 (Bruker, 2001)'
_computing_publication_material  'CIFTAB (Sheldrick, 2001)'
_computing_structure_refinement  'SHELXTL V6.10 (Bruker, 2001)'
_computing_structure_solution    'SHELXTL V6.10 (Bruker, 2001)'
_diffrn_ambient_temperature      193(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device       'Siemens Platform/CCD'
_diffrn_measurement_method       'profile data from \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_wavelength_id  p92xa
_diffrn_reflns_av_R_equivalents  0.1079
_diffrn_reflns_av_sigmaI/netI    0.1045
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       59
_diffrn_reflns_limit_l_min       -59
_diffrn_reflns_number            41373
_diffrn_reflns_theta_full        25.38
_diffrn_reflns_theta_max         25.38
_diffrn_reflns_theta_min         5.00
_diffrn_source                   'normal-focus sealed tube'
_diffrn_standards_decay_%        1.1
_diffrn_standards_interval_time  549
_diffrn_standards_number         417
_exptl_absorpt_coefficient_mu    0.241
_exptl_absorpt_correction_T_max  0.9714
_exptl_absorpt_correction_T_min  0.9009
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   '(Bruker, 2001)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.106
_exptl_crystal_description       columnar
_exptl_crystal_F_000             2412
_exptl_crystal_id                p92xa
_exptl_crystal_preparation
; 
The data crystal was mounted using oil (Parantone-N, Exxon) to a 
0.3 mm cryo-loop (Hampton Research) with the (0 0 -1) scattering planes 
roughly normal to the spindle axis. 
;
_exptl_crystal_recrystallization_method 'recrystallized from pentane at 0 C'
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.294
_refine_diff_density_min         -0.306
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.01(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.914
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     433
_refine_ls_number_reflns         7987
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.914
_refine_ls_R_factor_all          0.1037
_refine_ls_R_factor_gt           0.0514
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0473P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0903
_refine_ls_wR_factor_ref         0.1017
_reflns_number_gt                4830
_reflns_number_total             7987
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo052142nsi20051013_043143.cif
_cod_original_sg_symbol_Hall     'P 61 '
_cod_database_code               4021497