Highly stereoselective chlorination of beta-substituted cyclic alcohols using PPh3-NCS: factors that control the stereoselectivity.
Jaseer, E A; Naidu, Ajay B; Kumar, Sreehari S; Rao, R Koteshwar; Thakur, Krishna G; Sekar, G; Chemical communications (Cambridge, England)  (2007) 867–869; doi:10.1039/b614512d

data_7101743
_publ_section_title
;
 Highly stereoselective chlorination of beta-substituted cyclic
 alcohols using PPh3-NCS: factors that control the stereoselectivity.
;
_journal_issue                   8
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              867
_journal_page_last               869
_journal_paper_doi               10.1039/b614512d
_journal_year                    2007
_chemical_formula_sum            'C15 H19 N O5'
_chemical_formula_weight         293.31
_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_creation_method           SHELXL-97
_cell_angle_alpha                88.923(5)
_cell_angle_beta                 85.403(5)
_cell_angle_gamma                62.334(4)
_cell_formula_units_Z            2
_cell_length_a                   7.2564(6)
_cell_length_b                   7.4017(5)
_cell_length_c                   15.5988(13)
_cell_measurement_reflns_used    3328
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.2
_cell_measurement_theta_min      2.6
_cell_volume                     739.47(10)
_computing_cell_refinement       'APEX2/SAINT (BRUKER, 2004)'
_computing_data_collection       'APEX2 (BRUKER, 2004)'
_computing_data_reduction        'SAINT/XPREP (BRUKER, 2004)'
_computing_molecular_graphics    'ORTEP32 (WINGX)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (WINGX)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device_type  'Bruker axs (Kappa apex2)'
_diffrn_measurement_method       '\w and \f scan'
_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  0.0237
_diffrn_reflns_av_sigmaI/netI    0.0328
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            6693
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.31
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.95
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             312
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.464
_refine_diff_density_min         -0.517
_refine_diff_density_rms         0.171
_refine_ls_extinction_coef       0.111(16)
_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   1.199
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     206
_refine_ls_number_reflns         2530
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.199
_refine_ls_R_factor_all          0.0999
_refine_ls_R_factor_gt           0.0826
_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^)+(0.0951P)^2^+1.5884P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2441
_refine_ls_wR_factor_ref         0.2637
_reflns_number_gt                2033
_reflns_number_total             2530
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b614512d.txt
_cod_data_source_block           jaseer
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7101743