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_7101744
_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_moiety         'C12 H16 N2 O3'
_chemical_formula_sum            'C12 H16 N2 O3'
_chemical_formula_weight         236.27
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 122.342(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   18.6930(18)
_cell_length_b                   9.9424(8)
_cell_length_c                   14.9984(16)
_cell_measurement_reflns_used    4732
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      31.0
_cell_measurement_theta_min      2.4
_cell_volume                     2355.1(4)
_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    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  0.0220
_diffrn_reflns_av_sigmaI/netI    0.0200
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            16478
_diffrn_reflns_theta_full        32.23
_diffrn_reflns_theta_max         32.23
_diffrn_reflns_theta_min         2.42
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9230
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prisamatic
_exptl_crystal_F_000             1008
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.294
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.279
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         4148
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.279
_refine_ls_R_factor_all          0.0827
_refine_ls_R_factor_gt           0.0526
_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^)+(0.1000P)^2^+0.0194P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1701
_refine_ls_wR_factor_ref         0.1973
_reflns_number_gt                2723
_reflns_number_total             4148
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b614512d.txt
_cod_data_source_block           new
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
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_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               7101744